test_x509.py

# This file is dual licensed under the terms of the Apache License, Version
# 2.0, and the BSD License. See the LICENSE file in the root of this repository
# for complete details.


import binascii
import copy
import datetime
import ipaddress
import os
import typing

import pytest

from cryptography import utils, x509
from cryptography.exceptions import InvalidSignature, UnsupportedAlgorithm
from cryptography.hazmat.bindings._rust import test_support
from cryptography.hazmat.primitives import hashes, serialization
from cryptography.hazmat.primitives.asymmetric import (
    dh,
    dsa,
    ec,
    ed448,
    ed25519,
    mldsa,
    mlkem,
    padding,
    rsa,
    types,
    x448,
    x25519,
)
from cryptography.hazmat.primitives.asymmetric.utils import (
    decode_dss_signature,
)
from cryptography.x509.extensions import ExtendedKeyUsage
from cryptography.x509.name import _ASN1Type
from cryptography.x509.oid import (
    AuthorityInformationAccessOID,
    ExtendedKeyUsageOID,
    ExtensionOID,
    NameOID,
    PublicKeyAlgorithmOID,
    SignatureAlgorithmOID,
    SubjectInformationAccessOID,
)

from ..hazmat.primitives.fixtures_dsa import DSA_KEY_2048, DSA_KEY_3072
from ..hazmat.primitives.fixtures_ec import EC_KEY_SECP256R1
from ..hazmat.primitives.fixtures_rsa import (
    RSA_KEY_2048_ALT,
)
from ..hazmat.primitives.test_ec import (
    _skip_curve_unsupported,
    _skip_deterministic_ecdsa_unsupported,
)
from ..hazmat.primitives.test_rsa import rsa_key_512, rsa_key_2048
from ..utils import (
    load_nist_vectors,
    load_vectors_from_file,
    raises_unsupported_algorithm,
)

# Make ruff happy since we're importing fixtures that pytest patches in as
# func args
__all__ = ["rsa_key_512", "rsa_key_2048"]


class DummyExtension(x509.ExtensionType):
    oid = x509.ObjectIdentifier("1.2.3.4")


class FakeGeneralName(x509.GeneralName):
    def __init__(self, value):
        self._value = value

    @property
    def value(self):
        return self._value


T = typing.TypeVar("T")


def _load_cert(filename, loader: typing.Callable[..., T]) -> T:
    return load_vectors_from_file(
        filename=filename,
        loader=lambda pemfile: loader(pemfile.read()),
        mode="rb",
    )


def _generate_ca_and_leaf(
    issuer_private_key: types.CertificateIssuerPrivateKeyTypes,
    subject_private_key: types.CertificateIssuerPrivateKeyTypes,
):
    if isinstance(
        issuer_private_key,
        (
            ed25519.Ed25519PrivateKey,
            ed448.Ed448PrivateKey,
            mldsa.MLDSA44PrivateKey,
            mldsa.MLDSA65PrivateKey,
            mldsa.MLDSA87PrivateKey,
        ),
    ):
        hash_alg = None
    else:
        hash_alg = hashes.SHA256()

    builder = (
        x509.CertificateBuilder()
        .subject_name(
            x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
        )
        .issuer_name(
            x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
        )
        .public_key(issuer_private_key.public_key())
        .serial_number(1)
        .not_valid_before(datetime.datetime(2020, 1, 1))
        .not_valid_after(datetime.datetime(2030, 1, 1))
    )
    ca = builder.sign(issuer_private_key, hash_alg)
    builder = (
        x509.CertificateBuilder()
        .subject_name(
            x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "leaf")])
        )
        .issuer_name(
            x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
        )
        .public_key(subject_private_key.public_key())
        .serial_number(100)
        .not_valid_before(datetime.datetime(2020, 1, 1))
        .not_valid_after(datetime.datetime(2025, 1, 1))
    )
    cert = builder.sign(issuer_private_key, hash_alg)
    return ca, cert


def _break_cert_sig(cert: x509.Certificate) -> x509.Certificate:
    cert_bad_sig = bytearray(cert.public_bytes(serialization.Encoding.PEM))
    # Break the sig by mutating 5 bytes. That's the base64 representation
    # though so there's somewhere closer to 2**-32 probability of
    # not breaking the sig. Spin that roulette wheel.
    cert_bad_sig[-40:-35] = 90, 90, 90, 90, 90
    return x509.load_pem_x509_certificate(bytes(cert_bad_sig))


def _check_cert_times(
    cert: x509.Certificate,
    not_valid_before: typing.Optional[datetime.datetime],
    not_valid_after: typing.Optional[datetime.datetime],
) -> None:
    if not_valid_before:
        with pytest.warns(utils.DeprecatedIn42):
            assert cert.not_valid_before == not_valid_before
        assert cert.not_valid_before_utc == not_valid_before.replace(
            tzinfo=datetime.timezone.utc
        )
    if not_valid_after:
        with pytest.warns(utils.DeprecatedIn42):
            assert cert.not_valid_after == not_valid_after
        assert cert.not_valid_after_utc == not_valid_after.replace(
            tzinfo=datetime.timezone.utc
        )


def _check_crl_times(
    crl: x509.CertificateRevocationList,
    last_update: datetime.datetime,
    next_update: datetime.datetime,
) -> None:
    with pytest.warns(utils.DeprecatedIn42):
        assert crl.last_update == last_update
        assert crl.next_update == next_update

    assert crl.last_update_utc == last_update.replace(
        tzinfo=datetime.timezone.utc
    )
    assert crl.next_update_utc == next_update.replace(
        tzinfo=datetime.timezone.utc
    )


class TestCertificateRevocationList:
    def test_load_pem_crl(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        assert isinstance(crl, x509.CertificateRevocationList)
        fingerprint = binascii.hexlify(crl.fingerprint(hashes.SHA1()))
        assert fingerprint == b"191b3428bf9d0dafa4edd42bc98603e182614c57"
        assert isinstance(crl.signature_hash_algorithm, hashes.SHA256)
        assert (
            crl.signature_algorithm_oid
            == SignatureAlgorithmOID.RSA_WITH_SHA256
        )

    def test_load_der_crl(self):
        crl = _load_cert(
            os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
            x509.load_der_x509_crl,
        )

        assert isinstance(crl, x509.CertificateRevocationList)
        fingerprint = binascii.hexlify(crl.fingerprint(hashes.SHA1()))
        assert fingerprint == b"dd3db63c50f4c4a13e090f14053227cb1011a5ad"
        assert isinstance(crl.signature_hash_algorithm, hashes.SHA256)

    def test_load_large_crl(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_almost_10k.pem"),
            x509.load_pem_x509_crl,
        )
        assert len(crl) == 9999

    def test_empty_crl_no_sequence(self):
        # The SEQUENCE for revoked certificates is optional so let's
        # test that we handle it properly.
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_empty_no_sequence.der"),
            x509.load_der_x509_crl,
        )
        assert len(crl) == 0

        with pytest.raises(IndexError):
            crl[0]
        assert crl.get_revoked_certificate_by_serial_number(12) is None
        assert list(iter(crl)) == []

    def test_invalid_pem(self):
        with pytest.raises(ValueError):
            x509.load_pem_x509_crl(b"notacrl")

        pem_bytes = _load_cert(
            os.path.join("x509", "custom", "valid_signature_cert.pem"),
            lambda data: data,
        )
        with pytest.raises(ValueError):
            x509.load_pem_x509_crl(pem_bytes)

    def test_invalid_der(self):
        with pytest.raises(ValueError):
            x509.load_der_x509_crl(b"notacrl")

    def test_invalid_time(self):
        with pytest.raises(ValueError, match="TBSCertList::this_update"):
            _load_cert(
                os.path.join("x509", "custom", "crl_invalid_time.der"),
                x509.load_der_x509_crl,
            )

    def test_unknown_signature_algorithm(self):
        crl = _load_cert(
            os.path.join(
                "x509", "custom", "crl_md2_unknown_crit_entry_ext.pem"
            ),
            x509.load_pem_x509_crl,
        )

        with raises_unsupported_algorithm(None):
            crl.signature_hash_algorithm

    def test_invalid_version(self):
        with pytest.raises(x509.InvalidVersion):
            _load_cert(
                os.path.join("x509", "custom", "crl_bad_version.pem"),
                x509.load_pem_x509_crl,
            )

    def test_issuer(self):
        crl = _load_cert(
            os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
            x509.load_der_x509_crl,
        )

        assert isinstance(crl.issuer, x509.Name)
        assert list(crl.issuer) == [
            x509.NameAttribute(x509.OID_COUNTRY_NAME, "US"),
            x509.NameAttribute(
                x509.OID_ORGANIZATION_NAME, "Test Certificates 2011"
            ),
            x509.NameAttribute(x509.OID_COMMON_NAME, "Good CA"),
        ]
        assert crl.issuer.get_attributes_for_oid(x509.OID_COMMON_NAME) == [
            x509.NameAttribute(x509.OID_COMMON_NAME, "Good CA")
        ]

    def test_equality(self):
        crl1 = _load_cert(
            os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
            x509.load_der_x509_crl,
        )

        crl2 = _load_cert(
            os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
            x509.load_der_x509_crl,
        )

        crl3 = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        assert crl1 == crl2
        assert crl1 != crl3
        assert crl1 != object()

    def test_comparison(self):
        crl1 = _load_cert(
            os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
            x509.load_der_x509_crl,
        )
        with pytest.raises(TypeError):
            crl1 < crl1  # type: ignore[operator]

    def test_update_dates(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.warns(utils.DeprecatedIn42):
            assert isinstance(crl.next_update, datetime.datetime)
            assert isinstance(crl.last_update, datetime.datetime)
            assert crl.next_update.isoformat() == "2016-01-01T00:00:00"
            assert crl.last_update.isoformat() == "2015-01-01T00:00:00"

        assert isinstance(crl.next_update_utc, datetime.datetime)
        assert isinstance(crl.last_update_utc, datetime.datetime)
        assert crl.next_update_utc.isoformat() == "2016-01-01T00:00:00+00:00"
        assert crl.last_update_utc.isoformat() == "2015-01-01T00:00:00+00:00"

    def test_no_next_update(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_no_next_update.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.warns(utils.DeprecatedIn42):
            assert crl.next_update is None
        assert crl.next_update_utc is None

    def test_unrecognized_extension(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_unrecognized_extension.der"),
            x509.load_der_x509_crl,
        )
        unrecognized = x509.UnrecognizedExtension(
            x509.ObjectIdentifier("1.2.3.4.5"),
            b"abcdef",
        )
        ext = crl.extensions.get_extension_for_oid(unrecognized.oid)
        assert ext.value == unrecognized

    def test_revoked_cert_retrieval(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        for r in crl:
            assert isinstance(r, x509.RevokedCertificate)

        # Check that len() works for CRLs.
        assert len(crl) == 12
        it = iter(crl)
        assert len(typing.cast(typing.Sized, it)) == 12
        next(it)
        assert len(typing.cast(typing.Sized, it)) == 11

    def test_get_revoked_certificate_by_serial_number(self):
        crl = _load_cert(
            os.path.join(
                "x509", "PKITS_data", "crls", "LongSerialNumberCACRL.crl"
            ),
            x509.load_der_x509_crl,
        )
        serial_number = 725064303890588110203033396814564464046290047507
        revoked = crl.get_revoked_certificate_by_serial_number(serial_number)
        assert isinstance(revoked, x509.RevokedCertificate)
        assert revoked.serial_number == serial_number
        assert crl.get_revoked_certificate_by_serial_number(500) is None

    def test_revoked_cert_retrieval_retain_only_revoked(self):
        """
        This test attempts to trigger the crash condition described in
        https://github.com/pyca/cryptography/issues/2557
        PyPy does gc at its own pace, so it will only be reliable on CPython.
        """
        revoked = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )[11]
        with pytest.warns(utils.DeprecatedIn42):
            assert revoked.revocation_date == datetime.datetime(
                2015, 1, 1, 0, 0
            )
        assert revoked.revocation_date_utc == datetime.datetime(
            2015, 1, 1, 0, 0, tzinfo=datetime.timezone.utc
        )
        assert revoked.serial_number == 11

    def test_extensions(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_ian_aia_aki.pem"),
            x509.load_pem_x509_crl,
        )

        crl_number = crl.extensions.get_extension_for_oid(
            ExtensionOID.CRL_NUMBER
        )
        aki = crl.extensions.get_extension_for_class(
            x509.AuthorityKeyIdentifier
        )
        aia = crl.extensions.get_extension_for_class(
            x509.AuthorityInformationAccess
        )
        ian = crl.extensions.get_extension_for_class(
            x509.IssuerAlternativeName
        )
        assert crl_number.value == x509.CRLNumber(1)
        assert crl_number.critical is False
        assert aki.value == x509.AuthorityKeyIdentifier(
            key_identifier=(b"yu\xbb\x84:\xcb,\xdez\t\xbe1\x1bC\xbc\x1c*MSX"),
            authority_cert_issuer=None,
            authority_cert_serial_number=None,
        )
        assert aia.value == x509.AuthorityInformationAccess(
            [
                x509.AccessDescription(
                    AuthorityInformationAccessOID.CA_ISSUERS,
                    x509.DNSName("cryptography.io"),
                )
            ]
        )
        assert ian.value == x509.IssuerAlternativeName(
            [x509.UniformResourceIdentifier("https://cryptography.io")]
        )

    def test_delta_crl_indicator(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_delta_crl_indicator.pem"),
            x509.load_pem_x509_crl,
        )

        dci = crl.extensions.get_extension_for_oid(
            ExtensionOID.DELTA_CRL_INDICATOR
        )
        assert dci.value == x509.DeltaCRLIndicator(12345678901234567890)
        assert dci.critical is True

    def test_signature(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        assert crl.signature == binascii.unhexlify(
            b"536a5a0794f68267361e7bc2f19167a3e667a2ab141535616855d8deb2ba1af"
            b"9fd4546b1fe76b454eb436af7b28229fedff4634dfc9dd92254266219ae0ea8"
            b"75d9ff972e9a2da23d5945f073da18c50a4265bfed9ca16586347800ef49dd1"
            b"6856d7265f4f3c498a57f04dc04404e2bd2e2ada1f5697057aacef779a18371"
            b"c621edc9a5c2b8ec1716e8fa22feeb7fcec0ce9156c8d344aa6ae8d1a5d99d0"
            b"9386df36307df3b63c83908f4a61a0ff604c1e292ad63b349d1082ddd7ae1b7"
            b"c178bba995523ec6999310c54da5706549797bfb1230f5593ba7b4353dade4f"
            b"d2be13a57580a6eb20b5c4083f000abac3bf32cd8b75f23e4c8f4b3a79e1e2d"
            b"58a472b0"
        )

    def test_tbs_certlist_bytes(self):
        crl = _load_cert(
            os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
            x509.load_der_x509_crl,
        )

        ca_cert = _load_cert(
            os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
            x509.load_der_x509_certificate,
        )

        public_key = ca_cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert crl.signature_hash_algorithm is not None
        public_key.verify(
            crl.signature,
            crl.tbs_certlist_bytes,
            padding.PKCS1v15(),
            crl.signature_hash_algorithm,
        )

    def test_public_bytes_pem(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_empty.pem"),
            x509.load_pem_x509_crl,
        )

        # Encode it to PEM and load it back.
        crl = x509.load_pem_x509_crl(
            crl.public_bytes(
                encoding=serialization.Encoding.PEM,
            ),
        )

        assert len(crl) == 0
        _check_crl_times(
            crl,
            last_update=datetime.datetime(2015, 12, 20, 23, 44, 47),
            next_update=datetime.datetime(2015, 12, 28, 0, 44, 47),
        )

    def test_public_bytes_der(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        # Encode it to DER and load it back.
        crl = x509.load_der_x509_crl(
            crl.public_bytes(
                encoding=serialization.Encoding.DER,
            ),
        )

        assert len(crl) == 12
        _check_crl_times(
            crl,
            last_update=datetime.datetime(2015, 1, 1, 0, 0, 0),
            next_update=datetime.datetime(2016, 1, 1, 0, 0, 0),
        )

    @pytest.mark.parametrize(
        ("cert_path", "loader_func", "encoding"),
        [
            (
                os.path.join("x509", "custom", "crl_all_reasons.pem"),
                x509.load_pem_x509_crl,
                serialization.Encoding.PEM,
            ),
            (
                os.path.join("x509", "PKITS_data", "crls", "GoodCACRL.crl"),
                x509.load_der_x509_crl,
                serialization.Encoding.DER,
            ),
        ],
    )
    def test_public_bytes_match(self, cert_path, loader_func, encoding):
        crl_bytes = load_vectors_from_file(
            cert_path, lambda pemfile: pemfile.read(), mode="rb"
        )
        crl = loader_func(crl_bytes)
        serialized = crl.public_bytes(encoding)
        assert serialized == crl_bytes

    def test_public_bytes_invalid_encoding(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_empty.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.raises(TypeError):
            crl.public_bytes(typing.cast(typing.Any, "NotAnEncoding"))

    def test_verify_bad(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "invalid_signature_crl.pem"),
            x509.load_pem_x509_crl,
        )
        crt = _load_cert(
            os.path.join("x509", "custom", "invalid_signature_cert.pem"),
            x509.load_pem_x509_certificate,
        )

        public_key = crt.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert not crl.is_signature_valid(public_key)

    def test_load_inner_outer_mismatch(self):
        data = load_vectors_from_file(
            os.path.join("x509", "custom", "crl_inner_outer_mismatch.der"),
            lambda f: f.read(),
            mode="rb",
        )
        with pytest.raises(ValueError, match="Inner and outer"):
            x509.load_der_x509_crl(data)

    def test_verify_good(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "valid_signature_crl.pem"),
            x509.load_pem_x509_crl,
        )
        crt = _load_cert(
            os.path.join("x509", "custom", "valid_signature_cert.pem"),
            x509.load_pem_x509_certificate,
        )

        public_key = crt.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert crl.is_signature_valid(public_key)

    def test_verify_argument_must_be_a_public_key(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "valid_signature_crl.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.raises(TypeError):
            crl.is_signature_valid(typing.cast(typing.Any, "not a public key"))

        with pytest.raises(TypeError):
            crl.is_signature_valid(typing.cast(typing.Any, object))

    def test_crl_issuer_invalid_printable_string(self):
        data = _load_cert(
            os.path.join(
                "x509", "custom", "crl_issuer_invalid_printable_string.der"
            ),
            lambda v: v,
        )
        with pytest.raises(ValueError):
            x509.load_der_x509_crl(data)


class TestRevokedCertificate:
    def test_revoked_basics(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        for i, rev in enumerate(crl):
            assert isinstance(rev, x509.RevokedCertificate)
            assert isinstance(rev.serial_number, int)
            with pytest.warns(utils.DeprecatedIn42):
                assert isinstance(rev.revocation_date, datetime.datetime)
            assert isinstance(rev.revocation_date_utc, datetime.datetime)
            assert isinstance(rev.extensions, x509.Extensions)

            assert rev.serial_number == i
            with pytest.warns(utils.DeprecatedIn42):
                assert rev.revocation_date.isoformat() == "2015-01-01T00:00:00"
            assert (
                rev.revocation_date_utc.isoformat()
                == "2015-01-01T00:00:00+00:00"
            )

    def test_revoked_extensions(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        exp_issuer = [
            x509.DirectoryName(
                x509.Name(
                    [
                        x509.NameAttribute(x509.OID_COUNTRY_NAME, "US"),
                        x509.NameAttribute(
                            x509.OID_COMMON_NAME, "cryptography.io"
                        ),
                    ]
                )
            )
        ]

        # First revoked cert doesn't have extensions, test if it is handled
        # correctly.
        rev0 = crl[0]
        # It should return an empty Extensions object.
        assert isinstance(rev0.extensions, x509.Extensions)
        assert len(rev0.extensions) == 0
        with pytest.raises(x509.ExtensionNotFound):
            rev0.extensions.get_extension_for_oid(x509.OID_CRL_REASON)
        with pytest.raises(x509.ExtensionNotFound):
            rev0.extensions.get_extension_for_oid(x509.OID_CERTIFICATE_ISSUER)
        with pytest.raises(x509.ExtensionNotFound):
            rev0.extensions.get_extension_for_oid(x509.OID_INVALIDITY_DATE)

        # Test manual retrieval of extension values.
        rev1 = crl[1]
        assert isinstance(rev1.extensions, x509.Extensions)

        reason = rev1.extensions.get_extension_for_class(x509.CRLReason).value
        assert reason == x509.CRLReason(x509.ReasonFlags.unspecified)

        issuer = rev1.extensions.get_extension_for_class(
            x509.CertificateIssuer
        ).value
        assert issuer == x509.CertificateIssuer(exp_issuer)

        date = rev1.extensions.get_extension_for_class(
            x509.InvalidityDate
        ).value
        assert date == x509.InvalidityDate(datetime.datetime(2015, 1, 1, 0, 0))

        # Check if all reason flags can be found in the CRL.
        flags = set(x509.ReasonFlags)
        for rev in crl:
            try:
                r = rev.extensions.get_extension_for_class(x509.CRLReason)
            except x509.ExtensionNotFound:
                # Not all revoked certs have a reason extension.
                pass
            else:
                flags.discard(r.value.reason)

        assert len(flags) == 0

    def test_no_revoked_certs(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_empty.pem"),
            x509.load_pem_x509_crl,
        )
        assert len(crl) == 0

    def test_duplicate_entry_ext(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_dup_entry_ext.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.raises(x509.DuplicateExtension):
            crl[0].extensions

    def test_unsupported_crit_entry_ext(self):
        crl = _load_cert(
            os.path.join(
                "x509", "custom", "crl_md2_unknown_crit_entry_ext.pem"
            ),
            x509.load_pem_x509_crl,
        )

        ext = crl[0].extensions.get_extension_for_oid(
            x509.ObjectIdentifier("1.2.3.4")
        )
        assert isinstance(ext.value, x509.UnrecognizedExtension)
        assert ext.value.value == b"\n\x01\x00"

    def test_unsupported_reason(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_unsupported_reason.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.raises(ValueError):
            crl[0].extensions

    def test_invalid_cert_issuer_ext(self):
        crl = _load_cert(
            os.path.join(
                "x509", "custom", "crl_inval_cert_issuer_entry_ext.pem"
            ),
            x509.load_pem_x509_crl,
        )

        with pytest.raises(ValueError):
            crl[0].extensions

    def test_invalidity_date_fractional_seconds(self):
        # The InvalidityDate GeneralizedTime must be encoded as DER, so a
        # value carrying fractional seconds is rejected, in line with the
        # other X.509 time fields and this extension's own encoder.
        crl = _load_cert(
            os.path.join(
                "x509", "custom", "crl_inval_date_fractional_seconds.der"
            ),
            x509.load_der_x509_crl,
        )

        with pytest.raises(ValueError):
            crl[0].extensions

    def test_indexing(self):
        crl = _load_cert(
            os.path.join("x509", "custom", "crl_all_reasons.pem"),
            x509.load_pem_x509_crl,
        )

        with pytest.raises(IndexError):
            crl[-13]
        with pytest.raises(IndexError):
            crl[12]

        assert crl[-1].serial_number == crl[11].serial_number
        assert len(crl[2:4]) == 2
        assert crl[2:4][0].serial_number == crl[2].serial_number
        assert crl[2:4][1].serial_number == crl[3].serial_number

    def test_get_revoked_certificate_doesnt_reorder(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048
        last_update = datetime.datetime(2002, 1, 1, 12, 1)
        next_update = datetime.datetime(2030, 1, 1, 12, 1)
        builder = (
            x509.CertificateRevocationListBuilder()
            .issuer_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.COMMON_NAME, "cryptography.io CA"
                        )
                    ]
                )
            )
            .last_update(last_update)
            .next_update(next_update)
        )
        for i in [2, 500, 3, 49, 7, 1]:
            revoked_cert = (
                x509.RevokedCertificateBuilder()
                .serial_number(i)
                .revocation_date(datetime.datetime(2012, 1, 1, 1, 1))
                .build()
            )
            builder = builder.add_revoked_certificate(revoked_cert)
        crl = builder.sign(private_key, hashes.SHA256())
        assert crl[0].serial_number == 2
        assert crl[2].serial_number == 3
        # make sure get_revoked_certificate_by_serial_number doesn't affect
        # ordering after being invoked
        crl.get_revoked_certificate_by_serial_number(500)
        assert crl[0].serial_number == 2
        assert crl[2].serial_number == 3


class TestRSAECertificate:
    def test_load_cert_pub_key(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "ca", "rsae_ca.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        expected_pub_key = load_vectors_from_file(
            os.path.join("x509", "custom", "ca", "rsa_key.pem"),
            lambda pemfile: serialization.load_pem_private_key(
                pemfile.read(), None, unsafe_skip_rsa_key_validation=True
            ),
            mode="rb",
        ).public_key()
        assert isinstance(expected_pub_key, rsa.RSAPublicKey)
        pub_key = cert.public_key()
        assert isinstance(pub_key, rsa.RSAPublicKey)
        assert (
            cert.public_key_algorithm_oid
            == PublicKeyAlgorithmOID.RSAES_PKCS1_v1_5
        )
        assert pub_key == expected_pub_key
        pss = cert.signature_algorithm_parameters
        assert isinstance(pss, padding.PSS)
        assert isinstance(pss._mgf, padding.MGF1)
        assert isinstance(pss._mgf._algorithm, hashes.SHA256)
        assert pss._salt_length == 0x14
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)
        pub_key.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            pss,
            cert.signature_hash_algorithm,
        )


class TestRSAPSSCertificate:
    def test_load_cert_pub_key(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "rsa_pss_cert.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        expected_pub_key = _load_cert(
            os.path.join("asymmetric", "PKCS8", "rsa_pss_2048_pub.der"),
            serialization.load_der_public_key,
        )
        assert isinstance(expected_pub_key, rsa.RSAPublicKey)
        pub_key = cert.public_key()
        assert isinstance(pub_key, rsa.RSAPublicKey)
        assert (
            cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.RSASSA_PSS
        )
        assert pub_key == expected_pub_key
        pss = cert.signature_algorithm_parameters
        assert isinstance(pss, padding.PSS)
        assert isinstance(pss._mgf, padding.MGF1)
        assert isinstance(pss._mgf._algorithm, hashes.SHA256)
        assert pss._salt_length == 32
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)
        pub_key.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            pss,
            cert.signature_hash_algorithm,
        )

    def test_load_pss_cert_no_null(self):
        """
        This test verifies that PSS certs where the hash algorithm
        identifiers have no trailing null still load properly. LibreSSL
        generates certs like this.
        """
        cert = _load_cert(
            os.path.join("x509", "custom", "rsa_pss_sha256_no_null.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        pss = cert.signature_algorithm_parameters
        assert isinstance(pss, padding.PSS)
        assert isinstance(pss._mgf, padding.MGF1)
        assert isinstance(pss._mgf._algorithm, hashes.SHA256)
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)

    def test_load_pss_sha1_mgf1_sha1(self):
        cert = _load_cert(
            os.path.join("x509", "ee-pss-sha1-cert.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        pub_key = cert.public_key()
        assert isinstance(pub_key, rsa.RSAPublicKey)
        pss = cert.signature_algorithm_parameters
        assert isinstance(pss, padding.PSS)
        assert isinstance(pss._mgf, padding.MGF1)
        assert isinstance(pss._mgf._algorithm, hashes.SHA1)
        assert pss._salt_length == 20
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA1)

    def test_invalid_mgf(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "rsa_pss_cert_invalid_mgf.der"),
            x509.load_der_x509_certificate,
        )
        with pytest.raises(ValueError):
            cert.signature_algorithm_parameters

    def test_unsupported_mgf_hash(self):
        cert = _load_cert(
            os.path.join(
                "x509", "custom", "rsa_pss_cert_unsupported_mgf_hash.der"
            ),
            x509.load_der_x509_certificate,
        )
        with pytest.raises(UnsupportedAlgorithm):
            cert.signature_algorithm_parameters

    def test_no_sig_params(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "rsa_pss_cert_no_sig_params.der"),
            x509.load_der_x509_certificate,
        )
        with pytest.raises(ValueError):
            cert.signature_algorithm_parameters
        with pytest.raises(ValueError):
            cert.signature_hash_algorithm


class TestRSACertificate:
    def test_load_pem_cert(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        assert cert.serial_number == 11559813051657483483
        fingerprint = binascii.hexlify(cert.fingerprint(hashes.SHA1()))
        assert fingerprint == b"2b619ed04bfc9c3b08eb677d272192286a0947a8"
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA1)
        assert (
            cert.signature_algorithm_oid == SignatureAlgorithmOID.RSA_WITH_SHA1
        )
        assert isinstance(
            cert.signature_algorithm_parameters, padding.PKCS1v15
        )
        assert isinstance(cert.public_key(), rsa.RSAPublicKey)
        assert (
            cert.public_key_algorithm_oid
            == PublicKeyAlgorithmOID.RSAES_PKCS1_v1_5
        )

    def test_check_pkcs1_signature_algorithm_parameters(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "ca", "rsa_ca.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        assert isinstance(
            cert.signature_algorithm_parameters, padding.PKCS1v15
        )
        pk = cert.public_key()
        assert isinstance(pk, rsa.RSAPublicKey)
        assert cert.signature_hash_algorithm is not None
        pk.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            cert.signature_algorithm_parameters,
            cert.signature_hash_algorithm,
        )

    def test_load_legacy_pem_header(self):
        cert = _load_cert(
            os.path.join("x509", "cryptography.io.old_header.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)

    def test_load_with_other_sections(self):
        cert = _load_cert(
            os.path.join("x509", "cryptography.io.with_garbage.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)

        cert = _load_cert(
            os.path.join("x509", "cryptography.io.with_headers.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)

    def test_load_multiple_sections(self):
        # We match OpenSSL's behavior of loading the first cert
        # if there are multiple. Arguably this would ideally be an
        # error, but "load the first" is a common expectation.
        cert = _load_cert(
            os.path.join("x509", "cryptography.io.chain.pem"),
            x509.load_pem_x509_certificate,
        )
        cert2 = _load_cert(
            os.path.join("x509", "cryptography.io.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert == cert2

    def test_negative_serial_number(self):
        # We load certificates with negative serial numbers but on load
        # and on access of the attribute we raise a warning
        with pytest.warns(utils.DeprecatedIn36):
            cert = _load_cert(
                os.path.join("x509", "custom", "negative_serial.pem"),
                x509.load_pem_x509_certificate,
            )

        with pytest.warns(utils.DeprecatedIn36):
            assert cert.serial_number == -18008675309

    def test_country_jurisdiction_country_too_long(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "bad_country.pem"),
            x509.load_pem_x509_certificate,
        )
        # Both warnings are emitted during the first parse_name call (when
        # cert.subject is first accessed); subsequent accesses return the
        # cached Name object without re-parsing, so both checks must live
        # inside a single pytest.warns block.
        with pytest.warns(UserWarning):
            assert (
                cert.subject.get_attributes_for_oid(x509.NameOID.COUNTRY_NAME)[
                    0
                ].value
                == "too long"
            )
            assert (
                cert.subject.get_attributes_for_oid(
                    x509.NameOID.JURISDICTION_COUNTRY_NAME
                )[0].value
                == "also too long"
            )

    def test_alternate_rsa_with_sha1_oid(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "alternate-rsa-sha1-oid.der"),
            x509.load_der_x509_certificate,
        )
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA1)
        assert (
            cert.signature_algorithm_oid
            == SignatureAlgorithmOID._RSA_WITH_SHA1
        )
        assert isinstance(cert.public_key(), rsa.RSAPublicKey)
        assert (
            cert.public_key_algorithm_oid
            == PublicKeyAlgorithmOID.RSAES_PKCS1_v1_5
        )

    def test_load_bmpstring_explicittext(self):
        cert = _load_cert(
            os.path.join("x509", "accvraiz1.pem"),
            x509.load_pem_x509_certificate,
        )
        ext = cert.extensions.get_extension_for_class(x509.CertificatePolicies)
        et = ext.value[0].policy_qualifiers[0].explicit_text
        assert et == (
            "Autoridad de Certificación Raíz de la ACCV (Agencia "
            "de Tecnología y Certificación Electrónica, CIF Q4601"
            "156E). CPS en http://www.accv.es"
        )

    def test_load_der_cert(self):
        cert = _load_cert(
            os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
            x509.load_der_x509_certificate,
        )
        assert isinstance(cert, x509.Certificate)
        assert cert.serial_number == 2
        fingerprint = binascii.hexlify(cert.fingerprint(hashes.SHA1()))
        assert fingerprint == b"6f49779533d565e8b7c1062503eab41492c38e4d"
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)

    def test_signature(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.signature == binascii.unhexlify(
            b"8e0f72fcbebe4755abcaf76c8ce0bae17cde4db16291638e1b1ce04a93cdb4c"
            b"44a3486070986c5a880c14fdf8497e7d289b2630ccb21d24a3d1aa1b2d87482"
            b"07f3a1e16ccdf8daa8a7ea1a33d49774f513edf09270bd8e665b6300a10f003"
            b"66a59076905eb63cf10a81a0ca78a6ef3127f6cb2f6fb7f947fce22a30d8004"
            b"8c243ba2c1a54c425fe12310e8a737638f4920354d4cce25cbd9dea25e6a2fe"
            b"0d8579a5c8d929b9275be221975479f3f75075bcacf09526523b5fd67f7683f"
            b"3cda420fabb1e9e6fc26bc0649cf61bb051d6932fac37066bb16f55903dfe78"
            b"53dc5e505e2a10fbba4f9e93a0d3b53b7fa34b05d7ba6eef869bfc34b8e514f"
            b"d5419f75"
        )
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert len(cert.signature) == public_key.key_size // 8

    @pytest.mark.supported(
        only_if=lambda backend: backend.signature_hash_supported(
            hashes.SHA1()
        ),
        skip_message="Does not support SHA-1 signature.",
    )
    def test_tbs_certificate_bytes(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.tbs_certificate_bytes == binascii.unhexlify(
            b"308202d8a003020102020900a06cb4b955f7f4db300d06092a864886f70d010"
            b"10505003058310b3009060355040613024155311330110603550408130a536f"
            b"6d652d53746174653121301f060355040a1318496e7465726e6574205769646"
            b"769747320507479204c74643111300f0603550403130848656c6c6f20434130"
            b"1e170d3134313132363231343132305a170d3134313232363231343132305a3"
            b"058310b3009060355040613024155311330110603550408130a536f6d652d53"
            b"746174653121301f060355040a1318496e7465726e657420576964676974732"
            b"0507479204c74643111300f0603550403130848656c6c6f2043413082012230"
            b"0d06092a864886f70d01010105000382010f003082010a0282010100b03af70"
            b"2059e27f1e2284b56bbb26c039153bf81f295b73a49132990645ede4d2da0a9"
            b"13c42e7d38d3589a00d3940d194f6e6d877c2ef812da22a275e83d8be786467"
            b"48b4e7f23d10e873fd72f57a13dec732fc56ab138b1bb308399bb412cd73921"
            b"4ef714e1976e09603405e2556299a05522510ac4574db5e9cb2cf5f99e8f48c"
            b"1696ab3ea2d6d2ddab7d4e1b317188b76a572977f6ece0a4ad396f0150e7d8b"
            b"1a9986c0cb90527ec26ca56e2914c270d2a198b632fa8a2fda55079d3d39864"
            b"b6fb96ddbe331cacb3cb8783a8494ccccd886a3525078847ca01ca5f803e892"
            b"14403e8a4b5499539c0b86f7a0daa45b204a8e079d8a5b03db7ba1ba3d7011a"
            b"70203010001a381bc3081b9301d0603551d0e04160414d8e89dc777e4472656"
            b"f1864695a9f66b7b0400ae3081890603551d23048181307f8014d8e89dc777e"
            b"4472656f1864695a9f66b7b0400aea15ca45a3058310b300906035504061302"
            b"4155311330110603550408130a536f6d652d53746174653121301f060355040"
            b"a1318496e7465726e6574205769646769747320507479204c74643111300f06"
            b"03550403130848656c6c6f204341820900a06cb4b955f7f4db300c0603551d1"
            b"3040530030101ff"
        )
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert cert.signature_hash_algorithm is not None
        public_key.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            padding.PKCS1v15(),
            cert.signature_hash_algorithm,
        )

    def test_tbs_precertificate_bytes_duplicate_extensions_raises(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "two_basic_constraints.pem"),
            x509.load_pem_x509_certificate,
        )

        with pytest.raises(
            x509.DuplicateExtension,
            match=r"Duplicate 2\.5\.29\.19 extension found",
        ):
            cert.tbs_precertificate_bytes

    def test_tbs_precertificate_bytes_no_extensions_raises(self):
        cert = _load_cert(
            os.path.join("x509", "v1_cert.pem"),
            x509.load_pem_x509_certificate,
        )

        with pytest.raises(
            ValueError,
            match="Could not find pre-certificate SCT list extension",
        ):
            cert.tbs_precertificate_bytes

    def test_tbs_precertificate_bytes_missing_extension_raises(self):
        cert = _load_cert(
            os.path.join("x509", "cryptography.io.pem"),
            x509.load_pem_x509_certificate,
        )

        # This cert doesn't have an SCT list extension, so it will throw a
        # `ValueError` when we try to retrieve the property
        with pytest.raises(
            ValueError,
            match="Could not find pre-certificate SCT list extension",
        ):
            cert.tbs_precertificate_bytes

    def test_tbs_precertificate_bytes_strips_scts(self):
        cert = _load_cert(
            os.path.join("x509", "cryptography-scts.pem"),
            x509.load_pem_x509_certificate,
        )

        expected_tbs_precertificate_bytes = load_vectors_from_file(
            filename=os.path.join("x509", "cryptography-scts-tbs-precert.der"),
            loader=lambda data: data.read(),
            mode="rb",
        )
        assert (
            expected_tbs_precertificate_bytes == cert.tbs_precertificate_bytes
        )
        assert cert.tbs_precertificate_bytes != cert.tbs_certificate_bytes

    def test_issuer(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "Validpre2000UTCnotBeforeDateTest3EE.crt",
            ),
            x509.load_der_x509_certificate,
        )
        issuer = cert.issuer
        assert isinstance(issuer, x509.Name)
        assert list(issuer) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(
                NameOID.ORGANIZATION_NAME, "Test Certificates 2011"
            ),
            x509.NameAttribute(NameOID.COMMON_NAME, "Good CA"),
        ]
        assert issuer.get_attributes_for_oid(NameOID.COMMON_NAME) == [
            x509.NameAttribute(NameOID.COMMON_NAME, "Good CA")
        ]

    def test_all_issuer_name_types(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "all_supported_names.pem"),
            x509.load_pem_x509_certificate,
        )
        issuer = cert.issuer

        assert isinstance(issuer, x509.Name)
        assert list(issuer) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(NameOID.COUNTRY_NAME, "CA"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Illinois"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Chicago"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "Zero, LLC"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "One, LLC"),
            x509.NameAttribute(NameOID.COMMON_NAME, "common name 0"),
            x509.NameAttribute(NameOID.COMMON_NAME, "common name 1"),
            x509.NameAttribute(NameOID.ORGANIZATIONAL_UNIT_NAME, "OU 0"),
            x509.NameAttribute(NameOID.ORGANIZATIONAL_UNIT_NAME, "OU 1"),
            x509.NameAttribute(NameOID.DN_QUALIFIER, "dnQualifier0"),
            x509.NameAttribute(NameOID.DN_QUALIFIER, "dnQualifier1"),
            x509.NameAttribute(NameOID.SERIAL_NUMBER, "123"),
            x509.NameAttribute(NameOID.SERIAL_NUMBER, "456"),
            x509.NameAttribute(NameOID.TITLE, "Title 0"),
            x509.NameAttribute(NameOID.TITLE, "Title 1"),
            x509.NameAttribute(NameOID.SURNAME, "Surname 0"),
            x509.NameAttribute(NameOID.SURNAME, "Surname 1"),
            x509.NameAttribute(NameOID.GIVEN_NAME, "Given Name 0"),
            x509.NameAttribute(NameOID.GIVEN_NAME, "Given Name 1"),
            x509.NameAttribute(NameOID.PSEUDONYM, "Incognito 0"),
            x509.NameAttribute(NameOID.PSEUDONYM, "Incognito 1"),
            x509.NameAttribute(NameOID.GENERATION_QUALIFIER, "Last Gen"),
            x509.NameAttribute(NameOID.GENERATION_QUALIFIER, "Next Gen"),
            x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "dc0"),
            x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "dc1"),
            x509.NameAttribute(NameOID.EMAIL_ADDRESS, "test0@test.local"),
            x509.NameAttribute(NameOID.EMAIL_ADDRESS, "test1@test.local"),
        ]

    def test_subject(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "Validpre2000UTCnotBeforeDateTest3EE.crt",
            ),
            x509.load_der_x509_certificate,
        )
        subject = cert.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(
                NameOID.ORGANIZATION_NAME, "Test Certificates 2011"
            ),
            x509.NameAttribute(
                NameOID.COMMON_NAME,
                "Valid pre2000 UTC notBefore Date EE Certificate Test3",
            ),
        ]
        assert subject.get_attributes_for_oid(NameOID.COMMON_NAME) == [
            x509.NameAttribute(
                NameOID.COMMON_NAME,
                "Valid pre2000 UTC notBefore Date EE Certificate Test3",
            )
        ]

    def test_unicode_name(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "utf8_common_name.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.subject.get_attributes_for_oid(NameOID.COMMON_NAME) == [
            x509.NameAttribute(NameOID.COMMON_NAME, "We heart UTF8!\u2122")
        ]
        assert cert.issuer.get_attributes_for_oid(NameOID.COMMON_NAME) == [
            x509.NameAttribute(NameOID.COMMON_NAME, "We heart UTF8!\u2122")
        ]

    def test_invalid_unicode_name(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "invalid_utf8_common_name.pem"),
            x509.load_pem_x509_certificate,
        )
        with pytest.raises(ValueError, match="subject"):
            cert.subject
        with pytest.raises(ValueError, match="issuer"):
            cert.issuer

    def test_name_attribute_unsupported_type_tag(self):
        # A name attribute value whose ASN.1 tag is not one of the recognised
        # string types must raise a ValueError, not a bare KeyError.
        cert = _load_cert(
            os.path.join(
                "x509", "custom", "name_attribute_unsupported_tag.pem"
            ),
            x509.load_pem_x509_certificate,
        )
        with pytest.raises(ValueError, match="subject"):
            cert.subject
        with pytest.raises(ValueError, match="issuer"):
            cert.issuer

    def test_non_ascii_dns_name(self):
        cert = _load_cert(
            os.path.join("x509", "utf8-dnsname.pem"),
            x509.load_pem_x509_certificate,
        )
        san = cert.extensions.get_extension_for_class(
            x509.SubjectAlternativeName
        ).value

        names = san.get_values_for_type(x509.DNSName)

        assert names == [
            "partner.biztositas.hu",
            "biztositas.hu",
            "*.biztositas.hu",
            "biztos\xedt\xe1s.hu",
            "*.biztos\xedt\xe1s.hu",
            "xn--biztosts-fza2j.hu",
            "*.xn--biztosts-fza2j.hu",
        ]

    def test_all_subject_name_types(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "all_supported_names.pem"),
            x509.load_pem_x509_certificate,
        )
        subject = cert.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "AU"),
            x509.NameAttribute(NameOID.COUNTRY_NAME, "DE"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "California"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "New York"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "San Francisco"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Ithaca"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "Org Zero, LLC"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "Org One, LLC"),
            x509.NameAttribute(NameOID.COMMON_NAME, "CN 0"),
            x509.NameAttribute(NameOID.COMMON_NAME, "CN 1"),
            x509.NameAttribute(
                NameOID.ORGANIZATIONAL_UNIT_NAME, "Engineering 0"
            ),
            x509.NameAttribute(
                NameOID.ORGANIZATIONAL_UNIT_NAME, "Engineering 1"
            ),
            x509.NameAttribute(NameOID.DN_QUALIFIER, "qualified0"),
            x509.NameAttribute(NameOID.DN_QUALIFIER, "qualified1"),
            x509.NameAttribute(NameOID.SERIAL_NUMBER, "789"),
            x509.NameAttribute(NameOID.SERIAL_NUMBER, "012"),
            x509.NameAttribute(NameOID.TITLE, "Title IX"),
            x509.NameAttribute(NameOID.TITLE, "Title X"),
            x509.NameAttribute(NameOID.SURNAME, "Last 0"),
            x509.NameAttribute(NameOID.SURNAME, "Last 1"),
            x509.NameAttribute(NameOID.GIVEN_NAME, "First 0"),
            x509.NameAttribute(NameOID.GIVEN_NAME, "First 1"),
            x509.NameAttribute(NameOID.PSEUDONYM, "Guy Incognito 0"),
            x509.NameAttribute(NameOID.PSEUDONYM, "Guy Incognito 1"),
            x509.NameAttribute(NameOID.GENERATION_QUALIFIER, "32X"),
            x509.NameAttribute(NameOID.GENERATION_QUALIFIER, "Dreamcast"),
            x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "dc2"),
            x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "dc3"),
            x509.NameAttribute(NameOID.EMAIL_ADDRESS, "test2@test.local"),
            x509.NameAttribute(NameOID.EMAIL_ADDRESS, "test3@test.local"),
        ]

    def test_load_good_ca_cert(self):
        cert = _load_cert(
            os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
            x509.load_der_x509_certificate,
        )

        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(2010, 1, 1, 8, 30),
            not_valid_after=datetime.datetime(2030, 12, 31, 8, 30),
        )
        assert cert.serial_number == 2
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert cert.version is x509.Version.v3
        fingerprint = binascii.hexlify(cert.fingerprint(hashes.SHA1()))
        assert fingerprint == b"6f49779533d565e8b7c1062503eab41492c38e4d"

    def test_utc_pre_2000_not_before_cert(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "Validpre2000UTCnotBeforeDateTest3EE.crt",
            ),
            x509.load_der_x509_certificate,
        )

        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(1950, 1, 1, 12, 1),
            not_valid_after=None,
        )

    def test_pre_2000_utc_not_after_cert(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "Invalidpre2000UTCEEnotAfterDateTest7EE.crt",
            ),
            x509.load_der_x509_certificate,
        )

        _check_cert_times(
            cert,
            not_valid_before=None,
            not_valid_after=datetime.datetime(1999, 1, 1, 12, 1),
        )

    def test_post_2000_utc_cert(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(2014, 11, 26, 21, 41, 20),
            not_valid_after=datetime.datetime(2014, 12, 26, 21, 41, 20),
        )

    def test_generalized_time_not_before_cert(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "ValidGeneralizedTimenotBeforeDateTest4EE.crt",
            ),
            x509.load_der_x509_certificate,
        )
        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(2002, 1, 1, 12, 1),
            not_valid_after=datetime.datetime(2030, 12, 31, 8, 30),
        )
        assert cert.version is x509.Version.v3

    def test_generalized_time_not_after_cert(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "ValidGeneralizedTimenotAfterDateTest8EE.crt",
            ),
            x509.load_der_x509_certificate,
        )
        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(2010, 1, 1, 8, 30),
            not_valid_after=datetime.datetime(2050, 1, 1, 12, 1),
        )
        assert cert.version is x509.Version.v3

    def test_invalid_version_cert(self):
        with pytest.raises(x509.InvalidVersion) as exc:
            _load_cert(
                os.path.join("x509", "custom", "invalid_version.pem"),
                x509.load_pem_x509_certificate,
            )

        assert exc.value.parsed_version == 7

    def test_invalid_visiblestring_in_explicit_text(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "belgian-eid-invalid-visiblestring.pem",
            ),
            x509.load_pem_x509_certificate,
        )
        with pytest.warns(utils.DeprecatedIn41):
            cp = cert.extensions.get_extension_for_class(
                x509.CertificatePolicies
            ).value
        assert isinstance(cp, x509.CertificatePolicies)
        assert cp[0].policy_qualifiers[1].explicit_text == (
            "Gebruik onderworpen aan aansprakelijkheidsbeperkingen, zie CPS "
            "- Usage soumis à des limitations de responsabilité, voir CPS - "
            "Verwendung unterliegt Haftungsbeschränkungen, gemäss CPS"
        )

    def test_eq(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        cert2 = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert == cert2

    def test_ne(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        cert2 = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "ValidGeneralizedTimenotAfterDateTest8EE.crt",
            ),
            x509.load_der_x509_certificate,
        )
        assert cert != cert2
        assert cert != object()

    def test_ordering_unsupported(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        cert2 = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        with pytest.raises(TypeError, match="'>' not supported"):
            cert > cert2  # type: ignore[operator]

    def test_hash(self):
        cert1 = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        cert2 = _load_cert(
            os.path.join("x509", "custom", "post2000utctime.pem"),
            x509.load_pem_x509_certificate,
        )
        cert3 = _load_cert(
            os.path.join(
                "x509",
                "PKITS_data",
                "certs",
                "ValidGeneralizedTimenotAfterDateTest8EE.crt",
            ),
            x509.load_der_x509_certificate,
        )

        assert hash(cert1) == hash(cert2)
        assert hash(cert1) != hash(cert3)

    def test_version_1_cert(self):
        cert = _load_cert(
            os.path.join("x509", "v1_cert.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.version is x509.Version.v1

    def test_invalid_pem(self):
        with pytest.raises(ValueError, match="Unable to load"):
            x509.load_pem_x509_certificate(b"notacert")

        crl = load_vectors_from_file(
            filename=os.path.join("x509", "custom", "crl_empty.pem"),
            loader=lambda pemfile: pemfile.read(),
            mode="rb",
        )
        with pytest.raises(ValueError, match="Valid PEM but no"):
            x509.load_pem_x509_certificate(crl)

    def test_invalid_der(self):
        with pytest.raises(ValueError):
            x509.load_der_x509_certificate(b"notacert")

    def test_unsupported_signature_hash_algorithm_cert(self):
        cert = _load_cert(
            os.path.join("x509", "verisign_md2_root.pem"),
            x509.load_pem_x509_certificate,
        )
        with raises_unsupported_algorithm(None):
            cert.signature_hash_algorithm

    def test_public_bytes_pem(self):
        # Load an existing certificate.
        cert = _load_cert(
            os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
            x509.load_der_x509_certificate,
        )

        # Encode it to PEM and load it back.
        cert = x509.load_pem_x509_certificate(
            cert.public_bytes(
                encoding=serialization.Encoding.PEM,
            ),
        )

        # We should recover what we had to start with.
        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(2010, 1, 1, 8, 30),
            not_valid_after=datetime.datetime(2030, 12, 31, 8, 30),
        )
        assert cert.serial_number == 2
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert cert.version is x509.Version.v3
        fingerprint = binascii.hexlify(cert.fingerprint(hashes.SHA1()))
        assert fingerprint == b"6f49779533d565e8b7c1062503eab41492c38e4d"

    def test_public_bytes_der(self):
        # Load an existing certificate.
        cert = _load_cert(
            os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
            x509.load_der_x509_certificate,
        )

        # Encode it to DER and load it back.
        cert = x509.load_der_x509_certificate(
            cert.public_bytes(
                encoding=serialization.Encoding.DER,
            ),
        )

        # We should recover what we had to start with.
        _check_cert_times(
            cert,
            not_valid_before=datetime.datetime(2010, 1, 1, 8, 30),
            not_valid_after=datetime.datetime(2030, 12, 31, 8, 30),
        )
        assert cert.serial_number == 2
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert cert.version is x509.Version.v3
        fingerprint = binascii.hexlify(cert.fingerprint(hashes.SHA1()))
        assert fingerprint == b"6f49779533d565e8b7c1062503eab41492c38e4d"

    def test_public_bytes_invalid_encoding(self):
        cert = _load_cert(
            os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
            x509.load_der_x509_certificate,
        )

        with pytest.raises(TypeError):
            cert.public_bytes(typing.cast(typing.Any, "NotAnEncoding"))

    @pytest.mark.parametrize(
        ("cert_path", "loader_func", "encoding"),
        [
            (
                os.path.join("x509", "v1_cert.pem"),
                x509.load_pem_x509_certificate,
                serialization.Encoding.PEM,
            ),
            (
                os.path.join("x509", "PKITS_data", "certs", "GoodCACert.crt"),
                x509.load_der_x509_certificate,
                serialization.Encoding.DER,
            ),
        ],
    )
    def test_public_bytes_match(self, cert_path, loader_func, encoding):
        cert_bytes = load_vectors_from_file(
            cert_path, lambda pemfile: pemfile.read(), mode="rb"
        )
        cert = loader_func(cert_bytes)
        serialized = cert.public_bytes(encoding)
        assert serialized == cert_bytes

    def test_certificate_repr(self):
        cert = _load_cert(
            os.path.join("x509", "cryptography.io.pem"),
            x509.load_pem_x509_certificate,
        )
        assert repr(cert) == (
            "<Certificate(subject=<Name(CN=www.cryptography.io,OU=Domain "
            "Control Validated - RapidSSL(R),OU=See "
            "www.rapidssl.com/resources/cps (c)14,OU=GT48742965)>, ...)>"
        )

    def test_parse_tls_feature_extension(self):
        cert = _load_cert(
            os.path.join("x509", "tls-feature-ocsp-staple.pem"),
            x509.load_pem_x509_certificate,
        )
        ext = cert.extensions.get_extension_for_class(x509.TLSFeature)
        assert ext.critical is False
        assert ext.value == x509.TLSFeature(
            [x509.TLSFeatureType.status_request]
        )

    def test_verify_directly_issued_by_rsa_pss(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        subject_private_key = RSA_KEY_2048_ALT.private_key(
            unsafe_skip_rsa_key_validation=True
        )

        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .public_key(rsa_key_2048.public_key())
            .serial_number(1)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2030, 1, 1))
        )
        ca = builder.sign(rsa_key_2048, hashes.SHA256())
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "leaf")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .public_key(subject_private_key.public_key())
            .serial_number(100)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2025, 1, 1))
        )
        cert = builder.sign(
            rsa_key_2048,
            hashes.SHA256(),
            rsa_padding=padding.PSS(
                padding.MGF1(hashes.SHA256()),
                salt_length=padding.PSS.DIGEST_LENGTH,
            ),
        )
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_rsa(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = RSA_KEY_2048_ALT.private_key(
            unsafe_skip_rsa_key_validation=True
        )
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_rsa_bad_sig(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = RSA_KEY_2048_ALT.private_key(
            unsafe_skip_rsa_key_validation=True
        )
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert_bad_sig = _break_cert_sig(cert)
        with pytest.raises(InvalidSignature):
            cert_bad_sig.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_rsa_mismatched_inner_out_oid(self):
        cert = _load_cert(
            os.path.join(
                "x509", "custom", "mismatch_inner_outer_sig_algorithm.der"
            ),
            x509.load_der_x509_certificate,
        )
        with pytest.raises(ValueError) as exc:
            cert.verify_directly_issued_by(cert)

        assert str(exc.value) == (
            "Inner and outer signature algorithms do not match. This is an "
            "invalid certificate."
        )

    def test_verify_directly_issued_by_subject_issuer_mismatch(self):
        cert = _load_cert(
            os.path.join("x509", "cryptography.io.pem"),
            x509.load_pem_x509_certificate,
        )
        with pytest.raises(ValueError) as exc:
            cert.verify_directly_issued_by(cert)

        assert str(exc.value) == (
            "Issuer certificate subject does not match certificate issuer."
        )

    def test_verify_directly_issued_by_algorithm_mismatch(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = RSA_KEY_2048_ALT.private_key(
            unsafe_skip_rsa_key_validation=True
        )
        _, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        # We need a CA with the same issuer DN but diff signature algorithm
        secondary_issuer_key = ec.generate_private_key(ec.SECP256R1())
        ca2, _ = _generate_ca_and_leaf(
            secondary_issuer_key, subject_private_key
        )
        with pytest.raises(ValueError):
            cert.verify_directly_issued_by(ca2)

    @pytest.mark.supported(
        only_if=lambda backend: backend.x25519_supported(),
        skip_message="Requires OpenSSL with Ed25519 and X25519 support",
    )
    def test_verify_directly_issued_by_unsupported_key_type(self):
        private_key = ed25519.Ed25519PrivateKey.generate()
        x25519_public = x25519.X25519PrivateKey.generate().public_key()
        # Generate an ed25519 CA
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .public_key(private_key.public_key())
            .serial_number(1)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2030, 1, 1))
        )
        cert = builder.sign(private_key, None)
        # Make a cert with the right issuer name but the wrong public key
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "PyCA CA")])
            )
            .public_key(x25519_public)
            .serial_number(1)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2030, 1, 1))
        )
        leaf = builder.sign(private_key, None)

        with pytest.raises(TypeError):
            cert.verify_directly_issued_by(leaf)

    def test_admissions_extension(self):
        cert = _load_cert(
            os.path.join(
                "x509",
                "custom",
                "admissions_extension_optional_data_not_provided.pem",
            ),
            x509.load_pem_x509_certificate,
        )
        ext = cert.extensions.get_extension_for_class(x509.Admissions)
        assert ext.value == x509.Admissions(
            authority=x509.DirectoryName(
                value=x509.Name(
                    [
                        x509.NameAttribute(
                            oid=x509.NameOID.COUNTRY_NAME, value="DE"
                        ),
                        x509.NameAttribute(
                            oid=x509.NameOID.ORGANIZATION_NAME,
                            value="Elektronisches Gesundheitsberuferegister",
                        ),
                    ]
                )
            ),
            admissions=[
                x509.Admission(
                    admission_authority=x509.RegisteredID(
                        value=x509.NameOID.ORGANIZATION_NAME
                    ),
                    naming_authority=x509.NamingAuthority(
                        id=x509.ObjectIdentifier("1.2.276.0.76.4.223"),
                        url="",
                        text="Betriebsstätte GKV-Spitzenverband",
                    ),
                    profession_infos=[
                        x509.ProfessionInfo(
                            naming_authority=x509.NamingAuthority(
                                id=x509.ObjectIdentifier("1.2.276.0.76.4.225"),
                                url="https://example.com",
                                text=(
                                    "Betriebsstätte Deutscher "
                                    "Apothekerverband"
                                ),
                            ),
                            profession_items=["Ã\x84rztin/Arzt", ""],
                            profession_oids=[
                                x509.ObjectIdentifier("1.2.276.0.76.4.30"),
                                x509.ObjectIdentifier("1.2.276.0.76.4.31"),
                            ],
                            registration_number="9-999/99999999",
                            add_profession_info=(
                                b'\x16"additional profession info example'
                            ),
                        )
                    ],
                ),
                x509.Admission(
                    admission_authority=x509.OtherName(
                        type_id=x509.NameOID.COUNTRY_NAME,
                        value=b"\x04\x04\x13\x02DE",
                    ),
                    naming_authority=None,
                    profession_infos=[
                        x509.ProfessionInfo(
                            naming_authority=x509.NamingAuthority(
                                id=x509.ObjectIdentifier("1.2.276.0.76.4.227"),
                                url=None,
                                text=(
                                    "Betriebsstätte der Deutsche Krankenhaus "
                                    "TrustCenter und Informationsverarbeitung "
                                    "GmbH"
                                ),
                            ),
                            profession_items=["Krankenhaus"],
                            profession_oids=[
                                x509.ObjectIdentifier("1.2.276.0.76.4.53"),
                                x509.ObjectIdentifier("1.2.276.0.76.4.246"),
                            ],
                            registration_number="9.9.9-99999999",
                            add_profession_info=None,
                        ),
                        x509.ProfessionInfo(
                            naming_authority=None,
                            profession_items=[
                                "Krankenhaus",
                                "Betriebsstätte Geburtshilfe",
                            ],
                            profession_oids=[
                                x509.ObjectIdentifier("1.2.276.0.76.4.53")
                            ],
                            registration_number="",
                            add_profession_info=None,
                        ),
                    ],
                ),
                x509.Admission(
                    admission_authority=None,
                    naming_authority=None,
                    profession_infos=[
                        x509.ProfessionInfo(
                            naming_authority=None,
                            profession_items=[],
                            profession_oids=None,
                            registration_number=None,
                            add_profession_info=None,
                        )
                    ],
                ),
                x509.Admission(
                    admission_authority=None,
                    naming_authority=x509.NamingAuthority(None, None, None),
                    profession_infos=[],
                ),
                x509.Admission(
                    admission_authority=None,
                    naming_authority=None,
                    profession_infos=[],
                ),
            ],
        )

        cert = _load_cert(
            os.path.join(
                "x509",
                "custom",
                "admissions_extension_authority_not_provided.pem",
            ),
            x509.load_pem_x509_certificate,
        )
        ext = cert.extensions.get_extension_for_class(x509.Admissions)
        assert ext.value == x509.Admissions(authority=None, admissions=[])


class TestRSACertificateRequest:
    @pytest.mark.parametrize(
        ("path", "loader_func"),
        [
            [
                os.path.join("x509", "requests", "rsa_sha1.pem"),
                x509.load_pem_x509_csr,
            ],
            [
                os.path.join("x509", "requests", "rsa_sha1.der"),
                x509.load_der_x509_csr,
            ],
        ],
    )
    def test_load_rsa_certificate_request(self, path, loader_func):
        request = _load_cert(path, loader_func)
        assert isinstance(request.signature_hash_algorithm, hashes.SHA1)
        assert (
            request.signature_algorithm_oid
            == SignatureAlgorithmOID.RSA_WITH_SHA1
        )
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert (
            request.public_key_algorithm_oid
            == PublicKeyAlgorithmOID.RSAES_PKCS1_v1_5
        )
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
        ]
        extensions = request.extensions
        assert isinstance(extensions, x509.Extensions)
        assert list(extensions) == []

    def test_load_legacy_pem_header(self):
        cert = _load_cert(
            os.path.join("x509", "requests", "ec_sha256_old_header.pem"),
            x509.load_pem_x509_csr,
        )
        assert isinstance(cert, x509.CertificateSigningRequest)

    def test_invalid_pem(self):
        with pytest.raises(ValueError, match="Unable to load"):
            x509.load_pem_x509_csr(b"notacsr")

        crl = load_vectors_from_file(
            filename=os.path.join("x509", "custom", "crl_empty.pem"),
            loader=lambda pemfile: pemfile.read(),
            mode="rb",
        )
        with pytest.raises(ValueError, match="Valid PEM but no"):
            x509.load_pem_x509_csr(crl)

    @pytest.mark.parametrize(
        "loader_func", [x509.load_pem_x509_csr, x509.load_der_x509_csr]
    )
    def test_invalid_certificate_request(self, loader_func):
        with pytest.raises(ValueError):
            loader_func(b"notacsr")

    def test_unsupported_signature_hash_algorithm_request(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_md4.pem"),
            x509.load_pem_x509_csr,
        )
        with raises_unsupported_algorithm(None):
            request.signature_hash_algorithm

    def test_invalid_version(self):
        with pytest.raises(x509.InvalidVersion):
            _load_cert(
                os.path.join("x509", "requests", "bad-version.pem"),
                x509.load_pem_x509_csr,
            )

    def test_duplicate_extension(self):
        request = _load_cert(
            os.path.join("x509", "requests", "two_basic_constraints.pem"),
            x509.load_pem_x509_csr,
        )
        with pytest.raises(x509.DuplicateExtension) as exc:
            request.extensions

        assert exc.value.oid == ExtensionOID.BASIC_CONSTRAINTS

    def test_unsupported_critical_extension(self):
        request = _load_cert(
            os.path.join(
                "x509", "requests", "unsupported_extension_critical.pem"
            ),
            x509.load_pem_x509_csr,
        )
        ext = request.extensions.get_extension_for_oid(
            x509.ObjectIdentifier("1.2.3.4")
        )
        assert isinstance(ext.value, x509.UnrecognizedExtension)
        assert ext.value.value == b"value"

    def test_unsupported_extension(self):
        request = _load_cert(
            os.path.join("x509", "requests", "unsupported_extension.pem"),
            x509.load_pem_x509_csr,
        )
        extensions = request.extensions
        assert len(extensions) == 1
        assert extensions[0].oid == x509.ObjectIdentifier("1.2.3.4")
        assert extensions[0].value == x509.UnrecognizedExtension(
            x509.ObjectIdentifier("1.2.3.4"), b"value"
        )

    def test_no_extension_with_other_attributes(self):
        request = _load_cert(
            os.path.join("x509", "requests", "challenge-unstructured.pem"),
            x509.load_pem_x509_csr,
        )
        assert len(request.extensions) == 0

    def test_request_basic_constraints(self):
        request = _load_cert(
            os.path.join("x509", "requests", "basic_constraints.pem"),
            x509.load_pem_x509_csr,
        )
        extensions = request.extensions
        assert isinstance(extensions, x509.Extensions)
        assert list(extensions) == [
            x509.Extension(
                ExtensionOID.BASIC_CONSTRAINTS,
                True,
                x509.BasicConstraints(ca=True, path_length=1),
            ),
        ]

    def test_subject_alt_name(self):
        request = _load_cert(
            os.path.join("x509", "requests", "san_rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        ext = request.extensions.get_extension_for_class(
            x509.SubjectAlternativeName
        )
        assert list(ext.value) == [
            x509.DNSName("cryptography.io"),
            x509.DNSName("sub.cryptography.io"),
        ]

    def test_freeipa_bad_critical(self):
        csr = _load_cert(
            os.path.join("x509", "requests", "freeipa-bad-critical.pem"),
            x509.load_pem_x509_csr,
        )
        with pytest.raises(ValueError):
            csr.extensions

    def test_public_bytes_pem(self):
        # Load an existing CSR.
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )

        # Encode it to PEM and load it back.
        request = x509.load_pem_x509_csr(
            request.public_bytes(
                encoding=serialization.Encoding.PEM,
            ),
        )

        # We should recover what we had to start with.
        assert isinstance(request.signature_hash_algorithm, hashes.SHA1)
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
        ]

    def test_public_bytes_der(self):
        # Load an existing CSR.
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )

        # Encode it to DER and load it back.
        request = x509.load_der_x509_csr(
            request.public_bytes(
                encoding=serialization.Encoding.DER,
            ),
        )

        # We should recover what we had to start with.
        assert isinstance(request.signature_hash_algorithm, hashes.SHA1)
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
        ]

    def test_signature(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.signature == binascii.unhexlify(
            b"8364c86ffbbfe0bfc9a21f831256658ca8989741b80576d36f08a934603a43b1"
            b"837246d00167a518abb1de7b51a1e5b7ebea14944800818b1a923c804f120a0d"
            b"624f6310ef79e8612755c2b01dcc7f59dfdbce0db3f2630f185f504b8c17af80"
            b"cbd364fa5fda68337153930948226cd4638287a0aed6524d3006885c19028a1e"
            b"e2f5a91d6e77dbaa0b49996ee0a0c60b55b61bd080a08bb34aa7f3e07e91f37f"
            b"6a11645be2d8654c1570dcda145ed7cc92017f7d53225d7f283f3459ec5bda41"
            b"cf6dd75d43676c543483385226b7e4fa29c8739f1b0eaf199613593991979862"
            b"e36181e8c4c270c354b7f52c128db1b70639823324c7ea24791b7bc3d7005f3b"
        )

    @pytest.mark.supported(
        only_if=lambda backend: backend.signature_hash_supported(
            hashes.SHA1()
        ),
        skip_message="Does not support SHA-1 signature.",
    )
    def test_tbs_certrequest_bytes(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.tbs_certrequest_bytes == binascii.unhexlify(
            b"308201840201003057310b3009060355040613025553310e300c060355040813"
            b"055465786173310f300d0603550407130641757374696e310d300b060355040a"
            b"130450794341311830160603550403130f63727970746f6772617068792e696f"
            b"30820122300d06092a864886f70d01010105000382010f003082010a02820101"
            b"00a840a78460cb861066dfa3045a94ba6cf1b7ab9d24c761cffddcc2cb5e3f1d"
            b"c3e4be253e7039ef14fe9d6d2304f50d9f2e1584c51530ab75086f357138bff7"
            b"b854d067d1d5f384f1f2f2c39cc3b15415e2638554ef8402648ae3ef08336f22"
            b"b7ecc6d4331c2b21c3091a7f7a9518180754a646640b60419e4cc6f5c798110a"
            b"7f030a639fe87e33b4776dfcd993940ec776ab57a181ad8598857976dc303f9a"
            b"573ca619ab3fe596328e92806b828683edc17cc256b41948a2bfa8d047d2158d"
            b"3d8e069aa05fa85b3272abb1c4b4422b6366f3b70e642377b145cd6259e5d3e7"
            b"db048d51921e50766a37b1b130ee6b11f507d20a834001e8de16a92c14f2e964"
            b"a30203010001a000"
        )
        assert request.signature_hash_algorithm is not None
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        public_key.verify(
            request.signature,
            request.tbs_certrequest_bytes,
            padding.PKCS1v15(),
            request.signature_hash_algorithm,
        )

    def test_public_bytes_invalid_encoding(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )

        with pytest.raises(TypeError):
            request.public_bytes(typing.cast(typing.Any, "NotAnEncoding"))

    def test_signature_invalid(self):
        request = _load_cert(
            os.path.join("x509", "requests", "invalid_signature.pem"),
            x509.load_pem_x509_csr,
        )
        assert not request.is_signature_valid

    def test_signature_valid(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.is_signature_valid

    @pytest.mark.parametrize(
        ("request_path", "loader_func", "encoding"),
        [
            (
                os.path.join("x509", "requests", "rsa_sha1.pem"),
                x509.load_pem_x509_csr,
                serialization.Encoding.PEM,
            ),
            (
                os.path.join("x509", "requests", "rsa_sha1.der"),
                x509.load_der_x509_csr,
                serialization.Encoding.DER,
            ),
        ],
    )
    def test_public_bytes_match(self, request_path, loader_func, encoding):
        request_bytes = load_vectors_from_file(
            request_path, lambda pemfile: pemfile.read(), mode="rb"
        )
        request = loader_func(request_bytes)
        serialized = request.public_bytes(encoding)
        assert serialized == request_bytes

    def test_eq(self):
        request1 = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        request2 = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )

        assert request1 == request2

    def test_ne(self):
        request1 = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        request2 = _load_cert(
            os.path.join("x509", "requests", "san_rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )

        assert request1 != request2
        assert request1 != object()

    def test_ordering_unsupported(self):
        csr = _load_cert(
            os.path.join("x509", "requests", "rsa_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        csr2 = _load_cert(
            os.path.join("x509", "requests", "rsa_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        with pytest.raises(TypeError, match="'>' not supported"):
            csr > csr2  # type: ignore[operator]

    def test_hash(self):
        request1 = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        request2 = _load_cert(
            os.path.join("x509", "requests", "rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        request3 = _load_cert(
            os.path.join("x509", "requests", "san_rsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )

        assert hash(request1) == hash(request2)
        assert hash(request1) != hash(request3)

    @pytest.mark.parametrize(
        ("hashalg", "hashalg_oid"),
        [
            (hashes.SHA224, x509.SignatureAlgorithmOID.RSA_WITH_SHA224),
            (hashes.SHA256, x509.SignatureAlgorithmOID.RSA_WITH_SHA256),
            (hashes.SHA384, x509.SignatureAlgorithmOID.RSA_WITH_SHA384),
            (hashes.SHA512, x509.SignatureAlgorithmOID.RSA_WITH_SHA512),
            (hashes.SHA3_224, x509.SignatureAlgorithmOID.RSA_WITH_SHA3_224),
            (hashes.SHA3_256, x509.SignatureAlgorithmOID.RSA_WITH_SHA3_256),
            (hashes.SHA3_384, x509.SignatureAlgorithmOID.RSA_WITH_SHA3_384),
            (hashes.SHA3_512, x509.SignatureAlgorithmOID.RSA_WITH_SHA3_512),
        ],
    )
    def test_build_cert(
        self, rsa_key_2048: rsa.RSAPrivateKey, hashalg, hashalg_oid, backend
    ):
        if not backend.signature_hash_supported(hashalg()):
            pytest.skip(f"{hashalg} signature not supported")

        issuer_private_key = rsa_key_2048
        subject_private_key = rsa_key_2048

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name(
                    [
                        x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                        x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
                        x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
                        x509.NameAttribute(
                            NameOID.COMMON_NAME, "cryptography.io"
                        ),
                    ]
                )
            )
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                        x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
                        x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
                        x509.NameAttribute(
                            NameOID.COMMON_NAME, "cryptography.io"
                        ),
                    ]
                )
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashalg(), backend)

        assert cert.version is x509.Version.v3
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert (
            cert.public_key_algorithm_oid
            == PublicKeyAlgorithmOID.RSAES_PKCS1_v1_5
        )
        assert cert.signature_algorithm_oid == hashalg_oid
        assert type(cert.signature_hash_algorithm) is hashalg
        _check_cert_times(
            cert,
            not_valid_before=not_valid_before,
            not_valid_after=not_valid_after,
        )
        basic_constraints = cert.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is False
        assert basic_constraints.value.path_length is None
        subject_alternative_name = cert.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
        )
        assert isinstance(
            subject_alternative_name.value, x509.SubjectAlternativeName
        )
        assert list(subject_alternative_name.value) == [
            x509.DNSName("cryptography.io"),
        ]

    def test_build_cert_private_type_encoding(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = rsa_key_2048
        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)
        name = x509.Name(
            [
                x509.NameAttribute(
                    NameOID.STATE_OR_PROVINCE_NAME,
                    "Texas",
                    _ASN1Type.PrintableString,
                ),
                x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
                x509.NameAttribute(
                    NameOID.COMMON_NAME,
                    "cryptography.io",
                    _ASN1Type.IA5String,
                ),
            ]
        )
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(name)
            .subject_name(name)
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )
        cert = builder.sign(issuer_private_key, hashes.SHA256())

        for dn in (cert.subject, cert.issuer):
            assert (
                dn.get_attributes_for_oid(NameOID.STATE_OR_PROVINCE_NAME)[
                    0
                ]._type
                == _ASN1Type.PrintableString
            )
            assert (
                dn.get_attributes_for_oid(NameOID.STATE_OR_PROVINCE_NAME)[
                    0
                ]._type
                == _ASN1Type.PrintableString
            )
            assert (
                dn.get_attributes_for_oid(NameOID.LOCALITY_NAME)[0]._type
                == _ASN1Type.UTF8String
            )

    def test_build_cert_printable_string_country_name(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = rsa_key_2048

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name(
                    [
                        x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                        x509.NameAttribute(
                            NameOID.JURISDICTION_COUNTRY_NAME, "US"
                        ),
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                        x509.NameAttribute(
                            NameOID.JURISDICTION_COUNTRY_NAME, "US"
                        ),
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashes.SHA256())

        parsed = test_support.test_parse_certificate(
            cert.public_bytes(serialization.Encoding.DER)
        )

        # Check that each value was encoded as an ASN.1 PRINTABLESTRING.
        assert parsed.issuer_value_tags[0] == 0x13
        assert parsed.subject_value_tags[0] == 0x13
        assert parsed.issuer_value_tags[1] == 0x13
        assert parsed.subject_value_tags[1] == 0x13


class TestCertificateBuilder:
    def test_checks_for_unsupported_extensions(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(private_key.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(1999, 1, 1))
            .not_valid_after(datetime.datetime(2020, 1, 1))
            .add_extension(DummyExtension(), False)
        )

        with pytest.raises(NotImplementedError):
            builder.sign(private_key, hashes.SHA256())

    def test_encode_nonstandard_aia(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        aia = x509.AuthorityInformationAccess(
            [
                x509.AccessDescription(
                    x509.ObjectIdentifier("2.999.7"),
                    x509.UniformResourceIdentifier("http://example.com"),
                ),
            ]
        )

        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(private_key.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(1999, 1, 1))
            .not_valid_after(datetime.datetime(2020, 1, 1))
            .add_extension(aia, False)
        )

        builder.sign(private_key, hashes.SHA256())

    def test_encode_nonstandard_sia(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        sia = x509.SubjectInformationAccess(
            [
                x509.AccessDescription(
                    x509.ObjectIdentifier("2.999.7"),
                    x509.UniformResourceIdentifier("http://example.com"),
                ),
            ]
        )

        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(private_key.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(2015, 1, 1))
            .not_valid_after(datetime.datetime(2040, 1, 1))
            .add_extension(sia, False)
        )

        cert = builder.sign(private_key, hashes.SHA256())
        ext = cert.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_INFORMATION_ACCESS
        )
        assert ext.value == sia

    def test_subject_dn_asn1_types(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        name = x509.Name(
            [
                x509.NameAttribute(NameOID.COMMON_NAME, "mysite.com"),
                x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                x509.NameAttribute(NameOID.LOCALITY_NAME, "value"),
                x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "value"),
                x509.NameAttribute(NameOID.STREET_ADDRESS, "value"),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "value"),
                x509.NameAttribute(NameOID.ORGANIZATIONAL_UNIT_NAME, "value"),
                x509.NameAttribute(NameOID.SERIAL_NUMBER, "value"),
                x509.NameAttribute(NameOID.SURNAME, "value"),
                x509.NameAttribute(NameOID.GIVEN_NAME, "value"),
                x509.NameAttribute(NameOID.TITLE, "value"),
                x509.NameAttribute(NameOID.GENERATION_QUALIFIER, "value"),
                x509.NameAttribute(NameOID.X500_UNIQUE_IDENTIFIER, "value"),
                x509.NameAttribute(NameOID.DN_QUALIFIER, "value"),
                x509.NameAttribute(NameOID.PSEUDONYM, "value"),
                x509.NameAttribute(NameOID.USER_ID, "value"),
                x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "value"),
                x509.NameAttribute(NameOID.EMAIL_ADDRESS, "value"),
                x509.NameAttribute(NameOID.JURISDICTION_COUNTRY_NAME, "US"),
                x509.NameAttribute(
                    NameOID.JURISDICTION_LOCALITY_NAME, "value"
                ),
                x509.NameAttribute(
                    NameOID.JURISDICTION_STATE_OR_PROVINCE_NAME, "value"
                ),
                x509.NameAttribute(NameOID.BUSINESS_CATEGORY, "value"),
                x509.NameAttribute(NameOID.POSTAL_ADDRESS, "value"),
                x509.NameAttribute(NameOID.POSTAL_CODE, "value"),
            ]
        )
        cert = (
            x509.CertificateBuilder()
            .subject_name(name)
            .issuer_name(name)
            .public_key(private_key.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(1999, 1, 1))
            .not_valid_after(datetime.datetime(2020, 1, 1))
            .sign(private_key, hashes.SHA256())
        )

        for dn in (cert.subject, cert.issuer):
            for oid, asn1_type in TestNameAttribute.EXPECTED_TYPES:
                assert dn.get_attributes_for_oid(oid)[0]._type == asn1_type

    @pytest.mark.parametrize(
        ("not_valid_before", "not_valid_after"),
        [
            [datetime.datetime(1970, 2, 1), datetime.datetime(9999, 1, 1)],
            [datetime.datetime(1970, 2, 1), datetime.datetime(9999, 12, 31)],
        ],
    )
    def test_extreme_times(
        self,
        rsa_key_2048: rsa.RSAPrivateKey,
        not_valid_before,
        not_valid_after,
    ):
        private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(private_key.public_key())
            .serial_number(777)
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )
        cert = builder.sign(private_key, hashes.SHA256())
        _check_cert_times(
            cert,
            not_valid_before=not_valid_before,
            not_valid_after=not_valid_after,
        )
        parsed = test_support.test_parse_certificate(
            cert.public_bytes(serialization.Encoding.DER)
        )
        # UTC TIME
        assert parsed.not_before_tag == 0x17
        # GENERALIZED TIME
        assert parsed.not_after_tag == 0x18

    def test_rdns_preserve_iteration_order(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        """
        This test checks that RDN ordering is consistent when loading
        data from a certificate. Since the underlying RDN is an ASN.1
        set these values get lexicographically ordered on encode and
        the parsed value won't necessarily be in the same order as
        the originally provided list. However, we want to make sure
        that the order is always consistent since it confuses people
        when it isn't.
        """
        name = x509.Name(
            [
                x509.RelativeDistinguishedName(
                    [
                        x509.NameAttribute(NameOID.TITLE, "Test"),
                        x509.NameAttribute(NameOID.COMMON_NAME, "Multivalue"),
                        x509.NameAttribute(NameOID.SURNAME, "RDNs"),
                    ]
                ),
            ]
        )

        cert = (
            x509.CertificateBuilder()
            .serial_number(1)
            .issuer_name(name)
            .subject_name(name)
            .public_key(rsa_key_2048.public_key())
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2038, 1, 1))
            .sign(rsa_key_2048, hashes.SHA256())
        )
        loaded_cert = x509.load_pem_x509_certificate(
            cert.public_bytes(encoding=serialization.Encoding.PEM)
        )
        assert next(iter(loaded_cert.subject.rdns[0])) == x509.NameAttribute(
            NameOID.SURNAME, "RDNs"
        )

    @pytest.mark.parametrize(
        ("alg", "mgf_alg"),
        [
            (hashes.SHA512(), hashes.SHA256()),
            (hashes.SHA3_512(), hashes.SHA3_256()),
        ],
    )
    def test_sign_pss(
        self, rsa_key_2048: rsa.RSAPrivateKey, alg, mgf_alg, backend
    ):
        if not backend.signature_hash_supported(alg):
            pytest.skip(f"{alg} signature not supported")
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(rsa_key_2048.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2038, 1, 1))
        )
        pss = padding.PSS(
            mgf=padding.MGF1(mgf_alg), salt_length=alg.digest_size
        )
        cert = builder.sign(rsa_key_2048, alg, rsa_padding=pss)
        pk = cert.public_key()
        assert isinstance(pk, rsa.RSAPublicKey)
        assert isinstance(cert.signature_hash_algorithm, type(alg))
        cert_params = cert.signature_algorithm_parameters
        assert isinstance(cert_params, padding.PSS)
        assert cert_params._salt_length == pss._salt_length
        assert isinstance(cert_params._mgf, padding.MGF1)
        assert isinstance(cert_params._mgf._algorithm, type(mgf_alg))
        pk.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            cert_params,
            alg,
        )

    @pytest.mark.parametrize(
        ("padding_len", "computed_len"),
        [
            (padding.PSS.MAX_LENGTH, 222),
            (padding.PSS.DIGEST_LENGTH, 32),
        ],
    )
    def test_sign_pss_length_options(
        self,
        rsa_key_2048: rsa.RSAPrivateKey,
        padding_len,
        computed_len,
        backend,
    ):
        pss = padding.PSS(
            mgf=padding.MGF1(hashes.SHA256()), salt_length=padding_len
        )
        if not backend.rsa_padding_supported(pss):
            pytest.skip("PSS padding with these parameters not supported")
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(rsa_key_2048.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2038, 1, 1))
        )
        cert = builder.sign(rsa_key_2048, hashes.SHA256(), rsa_padding=pss)
        assert isinstance(cert.signature_algorithm_parameters, padding.PSS)
        assert cert.signature_algorithm_parameters._salt_length == computed_len

    def test_sign_pss_auto_unsupported(self, rsa_key_2048: rsa.RSAPrivateKey):
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(rsa_key_2048.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2038, 1, 1))
        )
        pss = padding.PSS(
            mgf=padding.MGF1(hashes.SHA256()), salt_length=padding.PSS.AUTO
        )
        with pytest.raises(TypeError):
            builder.sign(rsa_key_2048, hashes.SHA256(), rsa_padding=pss)

    def test_sign_invalid_padding(self, rsa_key_2048: rsa.RSAPrivateKey):
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(rsa_key_2048.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2038, 1, 1))
        )
        with pytest.raises(TypeError):
            builder.sign(
                rsa_key_2048,
                hashes.SHA256(),
                rsa_padding=typing.cast(typing.Any, b"notapadding"),
            )
        eckey = ec.generate_private_key(ec.SECP256R1())
        with pytest.raises(TypeError):
            builder.sign(
                eckey, hashes.SHA256(), rsa_padding=padding.PKCS1v15()
            )

    def test_sign_pss_hash_none(self, rsa_key_2048: rsa.RSAPrivateKey):
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(rsa_key_2048.public_key())
            .serial_number(777)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2038, 1, 1))
        )
        pss = padding.PSS(mgf=padding.MGF1(hashes.SHA256()), salt_length=32)
        with pytest.raises(TypeError):
            builder.sign(rsa_key_2048, None, rsa_padding=pss)

    def test_no_subject_name(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        with pytest.raises(ValueError):
            builder.sign(subject_private_key, hashes.SHA256())
        with pytest.raises(ValueError):
            builder.create_unsigned()

    def test_no_issuer_name(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        with pytest.raises(ValueError):
            builder.sign(subject_private_key, hashes.SHA256())
        with pytest.raises(ValueError):
            builder.create_unsigned()

    def test_no_public_key(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        with pytest.raises(ValueError):
            builder.sign(subject_private_key, hashes.SHA256())
        with pytest.raises(ValueError):
            builder.create_unsigned()

    def test_no_not_valid_before(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        with pytest.raises(ValueError):
            builder.sign(subject_private_key, hashes.SHA256())
        with pytest.raises(ValueError):
            builder.create_unsigned()

    def test_no_not_valid_after(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
        )
        with pytest.raises(ValueError):
            builder.sign(subject_private_key, hashes.SHA256())
        with pytest.raises(ValueError):
            builder.create_unsigned()

    def test_no_serial_number(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        with pytest.raises(ValueError):
            builder.sign(subject_private_key, hashes.SHA256())
        with pytest.raises(ValueError):
            builder.create_unsigned()

    def test_issuer_name_must_be_a_name_type(self):
        builder = x509.CertificateBuilder()

        with pytest.raises(TypeError):
            builder.issuer_name(typing.cast(typing.Any, "subject"))

        with pytest.raises(TypeError):
            builder.issuer_name(typing.cast(typing.Any, object))

    def test_issuer_name_may_only_be_set_once(self):
        name = x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        builder = x509.CertificateBuilder().issuer_name(name)

        with pytest.raises(ValueError):
            builder.issuer_name(name)

    def test_subject_name_must_be_a_name_type(self):
        builder = x509.CertificateBuilder()

        with pytest.raises(TypeError):
            builder.subject_name(typing.cast(typing.Any, "subject"))

        with pytest.raises(TypeError):
            builder.subject_name(typing.cast(typing.Any, object))

    def test_subject_name_may_only_be_set_once(self):
        name = x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        builder = x509.CertificateBuilder().subject_name(name)

        with pytest.raises(ValueError):
            builder.subject_name(name)

    def test_not_valid_before_after_not_valid_after(self):
        builder = x509.CertificateBuilder()

        builder = builder.not_valid_after(datetime.datetime(2002, 1, 1, 12, 1))
        with pytest.raises(ValueError):
            builder.not_valid_before(datetime.datetime(2003, 1, 1, 12, 1))

    def test_not_valid_after_before_not_valid_before(self):
        builder = x509.CertificateBuilder()

        builder = builder.not_valid_before(
            datetime.datetime(2002, 1, 1, 12, 1)
        )
        with pytest.raises(ValueError):
            builder.not_valid_after(datetime.datetime(2001, 1, 1, 12, 1))

    def test_public_key_must_be_public_key(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048
        builder = x509.CertificateBuilder()

        with pytest.raises(TypeError):
            builder.public_key(typing.cast(typing.Any, private_key))

    def test_public_key_may_only_be_set_once(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048
        public_key = private_key.public_key()
        builder = x509.CertificateBuilder().public_key(public_key)

        with pytest.raises(ValueError):
            builder.public_key(public_key)

    def test_public_key_rsa_pss_spki(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048
        cert = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(
                private_key.public_key(),
                rsa_padding=padding.PSS,
            )
            .serial_number(777)
            .not_valid_before(datetime.datetime(2020, 1, 1))
            .not_valid_after(datetime.datetime(2030, 1, 1))
            .sign(
                private_key,
                hashes.SHA256(),
                rsa_padding=padding.PSS(
                    mgf=padding.MGF1(hashes.SHA256()),
                    salt_length=padding.PSS.DIGEST_LENGTH,
                ),
            )
        )
        assert (
            cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.RSASSA_PSS
        )
        public_key = cert.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        assert public_key == private_key.public_key()
        # The SPKI AlgorithmIdentifier must be id-RSASSA-PSS with the
        # parameters absent.
        assert bytes.fromhex(
            "300b06092a864886f70d01010a"
        ) in cert.public_bytes(serialization.Encoding.DER)
        cert.verify_directly_issued_by(cert)

    def test_public_key_rsa_padding_must_be_pss_class(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        with pytest.raises(TypeError):
            x509.CertificateBuilder().public_key(
                rsa_key_2048.public_key(),
                rsa_padding=typing.cast(
                    typing.Any,
                    padding.PSS(
                        mgf=padding.MGF1(hashes.SHA256()),
                        salt_length=padding.PSS.DIGEST_LENGTH,
                    ),
                ),
            )

        with pytest.raises(TypeError):
            x509.CertificateBuilder().public_key(
                rsa_key_2048.public_key(),
                rsa_padding=typing.cast(typing.Any, padding.PKCS1v15),
            )

    def test_public_key_rsa_padding_requires_rsa_key(self):
        private_key = ec.generate_private_key(ec.SECP256R1())
        with pytest.raises(TypeError):
            x509.CertificateBuilder().public_key(
                private_key.public_key(),
                rsa_padding=padding.PSS,
            )

    def test_serial_number_must_be_an_integer_type(self):
        with pytest.raises(TypeError):
            x509.CertificateBuilder().serial_number(
                typing.cast(typing.Any, 10.0)
            )

    def test_serial_number_must_be_non_negative(self):
        with pytest.raises(ValueError):
            x509.CertificateBuilder().serial_number(-1)

    def test_serial_number_must_be_positive(self):
        with pytest.raises(ValueError):
            x509.CertificateBuilder().serial_number(0)

    def test_minimal_serial_number(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number(1)
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "RU")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "RU")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        cert = builder.sign(subject_private_key, hashes.SHA256())
        assert cert.serial_number == 1

    def test_biggest_serial_number(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048
        builder = (
            x509.CertificateBuilder()
            .serial_number((1 << 159) - 1)
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "RU")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "RU")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
        )
        cert = builder.sign(subject_private_key, hashes.SHA256())
        assert cert.serial_number == (1 << 159) - 1

    def test_serial_number_must_be_less_than_160_bits_long(self):
        with pytest.raises(ValueError):
            x509.CertificateBuilder().serial_number(1 << 159)

    def test_serial_number_may_only_be_set_once(self):
        builder = x509.CertificateBuilder().serial_number(10)

        with pytest.raises(ValueError):
            builder.serial_number(20)

    def test_aware_not_valid_after(self, rsa_key_2048: rsa.RSAPrivateKey):
        tz = datetime.timezone(datetime.timedelta(hours=-8))
        time = datetime.datetime(2012, 1, 16, 22, 43, tzinfo=tz)
        utc_time = datetime.datetime(2012, 1, 17, 6, 43)
        private_key = rsa_key_2048
        cert_builder = x509.CertificateBuilder().not_valid_after(time)
        cert_builder = (
            cert_builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(utc_time - datetime.timedelta(days=365))
        )

        cert = cert_builder.sign(private_key, hashes.SHA256())
        _check_cert_times(
            cert, not_valid_before=None, not_valid_after=utc_time
        )

    def test_earliest_time(self, rsa_key_2048: rsa.RSAPrivateKey):
        time = datetime.datetime(1950, 1, 1)
        private_key = rsa_key_2048
        cert_builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(time)
            .not_valid_after(time)
        )
        cert = cert_builder.sign(private_key, hashes.SHA256())
        _check_cert_times(cert, not_valid_before=time, not_valid_after=time)
        parsed = test_support.test_parse_certificate(
            cert.public_bytes(serialization.Encoding.DER)
        )
        # UTC TIME
        assert parsed.not_before_tag == 0x17
        assert parsed.not_after_tag == 0x17

    def test_invalid_not_valid_after(self):
        with pytest.raises(TypeError):
            x509.CertificateBuilder().not_valid_after(
                typing.cast(typing.Any, 104204304504)
            )

        with pytest.raises(TypeError):
            x509.CertificateBuilder().not_valid_after(
                typing.cast(typing.Any, datetime.time())
            )

        with pytest.raises(ValueError):
            x509.CertificateBuilder().not_valid_after(
                datetime.datetime(1940, 8, 10)
            )

    def test_not_valid_after_may_only_be_set_once(self):
        builder = x509.CertificateBuilder().not_valid_after(
            datetime.datetime.now()
        )

        with pytest.raises(ValueError):
            builder.not_valid_after(datetime.datetime.now())

    def test_aware_not_valid_before(self, rsa_key_2048: rsa.RSAPrivateKey):
        tz = datetime.timezone(datetime.timedelta(hours=-8))
        time = datetime.datetime(2012, 1, 16, 22, 43, tzinfo=tz)
        utc_time = datetime.datetime(2012, 1, 17, 6, 43)
        private_key = rsa_key_2048
        cert_builder = x509.CertificateBuilder().not_valid_before(time)
        cert_builder = (
            cert_builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_after(utc_time + datetime.timedelta(days=366))
        )

        cert = cert_builder.sign(private_key, hashes.SHA256())
        _check_cert_times(
            cert, not_valid_before=utc_time, not_valid_after=None
        )

    def test_invalid_not_valid_before(self):
        with pytest.raises(TypeError):
            x509.CertificateBuilder().not_valid_before(
                typing.cast(typing.Any, 104204304504)
            )

        with pytest.raises(TypeError):
            x509.CertificateBuilder().not_valid_before(
                typing.cast(typing.Any, datetime.time())
            )

        with pytest.raises(ValueError):
            x509.CertificateBuilder().not_valid_before(
                datetime.datetime(1940, 8, 10)
            )

    def test_not_valid_before_may_only_be_set_once(self):
        builder = x509.CertificateBuilder().not_valid_before(
            datetime.datetime.now()
        )

        with pytest.raises(ValueError):
            builder.not_valid_before(datetime.datetime.now())

    def test_add_extension_checks_for_duplicates(self):
        builder = x509.CertificateBuilder().add_extension(
            x509.BasicConstraints(ca=False, path_length=None),
            True,
        )

        with pytest.raises(ValueError):
            builder.add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )

    def test_add_invalid_extension_type(self):
        builder = x509.CertificateBuilder()

        with pytest.raises(TypeError):
            builder.add_extension(
                typing.cast(typing.Any, object()),
                False,
            )

    @pytest.mark.parametrize("algorithm", [object(), None])
    def test_sign_with_unsupported_hash(
        self, rsa_key_2048: rsa.RSAPrivateKey, algorithm
    ):
        private_key = rsa_key_2048
        builder = x509.CertificateBuilder()
        builder = (
            builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )

        with pytest.raises(TypeError):
            builder.sign(private_key, algorithm)

    def test_sign_with_unsupported_hash_ed25519(self):
        private_key = ed25519.Ed25519PrivateKey.generate()
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    @pytest.mark.supported(
        only_if=lambda backend: backend.ed448_supported(),
        skip_message="Requires OpenSSL with Ed448 support",
    )
    def test_sign_with_unsupported_hash_ed448(self):
        private_key = ed448.Ed448PrivateKey.generate()
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    @pytest.mark.supported(
        only_if=lambda backend: backend.mldsa_supported(),
        skip_message="Requires a backend with ML-DSA support",
    )
    @pytest.mark.parametrize(
        "priv_key_cls",
        [
            mldsa.MLDSA44PrivateKey,
            mldsa.MLDSA65PrivateKey,
            mldsa.MLDSA87PrivateKey,
        ],
    )
    def test_sign_with_unsupported_hash_mldsa(self, priv_key_cls):
        private_key = priv_key_cls.generate()
        builder = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    @pytest.mark.supported(
        only_if=lambda backend: backend.hash_supported(hashes.MD5()),
        skip_message="Requires OpenSSL with MD5 support",
    )
    @pytest.mark.supported(
        only_if=lambda backend: backend.dsa_supported(),
        skip_message="Does not support DSA.",
    )
    @pytest.mark.parametrize(
        "hash_algorithm",
        [
            hashes.MD5(),
            hashes.SHA3_224(),
            hashes.SHA3_256(),
            hashes.SHA3_384(),
            hashes.SHA3_512(),
        ],
    )
    def test_sign_dsa_with_unsupported_hash(self, hash_algorithm):
        private_key = DSA_KEY_2048.private_key()
        builder = x509.CertificateBuilder()
        builder = (
            builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )
        with pytest.raises(UnsupportedAlgorithm):
            builder.sign(private_key, hash_algorithm)

    @pytest.mark.supported(
        only_if=lambda backend: backend.hash_supported(hashes.MD5()),
        skip_message="Requires OpenSSL with MD5 support",
    )
    def test_sign_ec_with_md5(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        private_key = EC_KEY_SECP256R1.private_key(backend)
        builder = x509.CertificateBuilder()
        builder = (
            builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )
        with pytest.raises(UnsupportedAlgorithm):
            builder.sign(
                private_key,
                typing.cast(typing.Any, hashes.MD5()),
                backend,
            )

    @pytest.mark.supported(
        only_if=lambda backend: backend.dsa_supported(),
        skip_message="Does not support DSA.",
    )
    @pytest.mark.parametrize(
        ("hashalg", "hashalg_oid"),
        [
            (hashes.SHA224, x509.SignatureAlgorithmOID.DSA_WITH_SHA224),
            (hashes.SHA256, x509.SignatureAlgorithmOID.DSA_WITH_SHA256),
            (hashes.SHA384, x509.SignatureAlgorithmOID.DSA_WITH_SHA384),
            (hashes.SHA512, x509.SignatureAlgorithmOID.DSA_WITH_SHA512),
        ],
    )
    def test_build_cert_with_dsa_private_key(self, hashalg, hashalg_oid):
        issuer_private_key = DSA_KEY_2048.private_key()
        subject_private_key = DSA_KEY_2048.private_key()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashalg())

        assert cert.version is x509.Version.v3
        assert cert.signature_algorithm_oid == hashalg_oid
        public_key = cert.public_key()
        assert isinstance(public_key, dsa.DSAPublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.DSA
        _check_cert_times(
            cert,
            not_valid_before=not_valid_before,
            not_valid_after=not_valid_after,
        )
        basic_constraints = cert.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is False
        assert basic_constraints.value.path_length is None
        subject_alternative_name = cert.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
        )
        assert isinstance(
            subject_alternative_name.value, x509.SubjectAlternativeName
        )
        assert list(subject_alternative_name.value) == [
            x509.DNSName("cryptography.io"),
        ]

    @pytest.mark.parametrize(
        ("hashalg", "hashalg_oid"),
        [
            (hashes.SHA224, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA224),
            (hashes.SHA256, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA256),
            (hashes.SHA384, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA384),
            (hashes.SHA512, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA512),
            (hashes.SHA3_224, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA3_224),
            (hashes.SHA3_256, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA3_256),
            (hashes.SHA3_384, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA3_384),
            (hashes.SHA3_512, x509.SignatureAlgorithmOID.ECDSA_WITH_SHA3_512),
        ],
    )
    def test_build_cert_with_ec_private_key(
        self, hashalg, hashalg_oid, backend
    ):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        if not backend.signature_hash_supported(hashalg()):
            pytest.skip(f"{hashalg} signature not supported")

        issuer_private_key = ec.generate_private_key(ec.SECP256R1(), backend)
        subject_private_key = ec.generate_private_key(ec.SECP256R1(), backend)

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashalg(), backend)

        assert cert.version is x509.Version.v3
        public_key = cert.public_key()
        assert isinstance(public_key, ec.EllipticCurvePublicKey)
        assert (
            cert.public_key_algorithm_oid
            == PublicKeyAlgorithmOID.EC_PUBLIC_KEY
        )
        assert cert.signature_algorithm_oid == hashalg_oid
        assert type(cert.signature_hash_algorithm) is hashalg
        _check_cert_times(
            cert,
            not_valid_before=not_valid_before,
            not_valid_after=not_valid_after,
        )
        basic_constraints = cert.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is False
        assert basic_constraints.value.path_length is None
        subject_alternative_name = cert.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
        )
        assert isinstance(
            subject_alternative_name.value, x509.SubjectAlternativeName
        )
        assert list(subject_alternative_name.value) == [
            x509.DNSName("cryptography.io"),
        ]

    def test_build_cert_with_deterministic_ecdsa_signature(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        _skip_deterministic_ecdsa_unsupported(backend)

        private_key = ec.generate_private_key(ec.SECP256R1())

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(x509.Name([]))
            .subject_name(x509.Name([]))
            .public_key(private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )
        cert1 = builder.sign(
            private_key,
            hashes.SHA256(),
            backend,
            ecdsa_deterministic=True,
        )
        cert2 = builder.sign(
            private_key,
            hashes.SHA256(),
            backend,
            ecdsa_deterministic=True,
        )
        cert_nondet = builder.sign(private_key, hashes.SHA256(), backend)
        cert_nondet2 = builder.sign(
            private_key, hashes.SHA256(), backend, ecdsa_deterministic=False
        )

        assert cert1.signature == cert2.signature
        assert cert1.signature != cert_nondet.signature
        assert cert_nondet.signature != cert_nondet2.signature

        private_key.public_key().verify(
            cert1.signature,
            cert1.tbs_certificate_bytes,
            ec.ECDSA(hashes.SHA256()),
        )

    def test_sign_deterministic_wrong_key_type(self, rsa_key_2048):
        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(x509.Name([]))
            .subject_name(x509.Name([]))
            .public_key(rsa_key_2048.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )
        with pytest.raises(TypeError):
            builder.sign(
                rsa_key_2048, hashes.SHA256(), ecdsa_deterministic=True
            )

    def test_build_cert_with_bmpstring_universalstring_name(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048
        issuer = x509.Name(
            [
                x509.NameAttribute(
                    NameOID.COMMON_NAME,
                    "cryptography.io",
                    _ASN1Type.BMPString,
                ),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            ]
        )
        subject = x509.Name(
            [
                x509.NameAttribute(
                    NameOID.COMMON_NAME,
                    "cryptography.io",
                    _ASN1Type.UniversalString,
                ),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            ]
        )
        builder = x509.CertificateBuilder()
        builder = (
            builder.subject_name(subject)
            .issuer_name(issuer)
            .serial_number(1)
            .public_key(private_key.public_key())
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2032, 1, 1, 12, 1))
        )
        cert = builder.sign(private_key, hashes.SHA256())
        assert cert.issuer == issuer
        assert cert.subject == subject

    def test_build_cert_with_ed25519(self):
        issuer_private_key = ed25519.Ed25519PrivateKey.generate()
        subject_private_key = ed25519.Ed25519PrivateKey.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, None)
        issuer_private_key.public_key().verify(
            cert.signature, cert.tbs_certificate_bytes
        )
        assert cert.signature_algorithm_oid == SignatureAlgorithmOID.ED25519
        assert cert.signature_hash_algorithm is None
        assert isinstance(cert.public_key(), ed25519.Ed25519PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ED25519
        assert cert.version is x509.Version.v3
        _check_cert_times(
            cert,
            not_valid_before=not_valid_before,
            not_valid_after=not_valid_after,
        )
        basic_constraints = cert.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is False
        assert basic_constraints.value.path_length is None
        subject_alternative_name = cert.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
        )
        assert isinstance(
            subject_alternative_name.value, x509.SubjectAlternativeName
        )
        assert list(subject_alternative_name.value) == [
            x509.DNSName("cryptography.io"),
        ]

    def test_build_cert_with_public_ed25519_rsa_sig(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = ed25519.Ed25519PrivateKey.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashes.SHA256())
        assert cert.signature_hash_algorithm is not None
        issuer_private_key.public_key().verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            padding.PKCS1v15(),
            cert.signature_hash_algorithm,
        )
        assert cert.signature_algorithm_oid == (
            SignatureAlgorithmOID.RSA_WITH_SHA256
        )
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)
        assert isinstance(cert.public_key(), ed25519.Ed25519PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ED25519

    @pytest.mark.supported(
        only_if=lambda backend: backend.ed448_supported(),
        skip_message="Requires OpenSSL with Ed448 support",
    )
    def test_build_cert_with_ed448(self):
        issuer_private_key = ed448.Ed448PrivateKey.generate()
        subject_private_key = ed448.Ed448PrivateKey.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, None)
        issuer_private_key.public_key().verify(
            cert.signature, cert.tbs_certificate_bytes
        )
        assert cert.signature_algorithm_oid == SignatureAlgorithmOID.ED448
        assert cert.signature_hash_algorithm is None
        assert isinstance(cert.public_key(), ed448.Ed448PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ED448
        assert cert.version is x509.Version.v3
        _check_cert_times(
            cert,
            not_valid_before=not_valid_before,
            not_valid_after=not_valid_after,
        )
        basic_constraints = cert.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is False
        assert basic_constraints.value.path_length is None
        subject_alternative_name = cert.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
        )
        assert isinstance(
            subject_alternative_name.value, x509.SubjectAlternativeName
        )
        assert list(subject_alternative_name.value) == [
            x509.DNSName("cryptography.io"),
        ]

    @pytest.mark.supported(
        only_if=lambda backend: backend.ed448_supported(),
        skip_message="Requires OpenSSL with Ed448 support",
    )
    def test_build_cert_with_public_ed448_rsa_sig(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = ed448.Ed448PrivateKey.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashes.SHA256())
        assert cert.signature_hash_algorithm is not None
        issuer_private_key.public_key().verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            padding.PKCS1v15(),
            cert.signature_hash_algorithm,
        )
        assert cert.signature_algorithm_oid == (
            SignatureAlgorithmOID.RSA_WITH_SHA256
        )
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)
        assert isinstance(cert.public_key(), ed448.Ed448PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ED448

    @pytest.mark.supported(
        only_if=lambda backend: backend.mldsa_supported(),
        skip_message="Requires a backend with ML-DSA support",
    )
    @pytest.mark.parametrize(
        ("priv_key_cls", "pub_key_cls", "sig_oid", "pub_oid"),
        [
            (
                mldsa.MLDSA44PrivateKey,
                mldsa.MLDSA44PublicKey,
                SignatureAlgorithmOID.ML_DSA_44,
                PublicKeyAlgorithmOID.ML_DSA_44,
            ),
            (
                mldsa.MLDSA65PrivateKey,
                mldsa.MLDSA65PublicKey,
                SignatureAlgorithmOID.ML_DSA_65,
                PublicKeyAlgorithmOID.ML_DSA_65,
            ),
            (
                mldsa.MLDSA87PrivateKey,
                mldsa.MLDSA87PublicKey,
                SignatureAlgorithmOID.ML_DSA_87,
                PublicKeyAlgorithmOID.ML_DSA_87,
            ),
        ],
    )
    def test_build_cert_with_mldsa(
        self, priv_key_cls, pub_key_cls, sig_oid, pub_oid
    ):
        issuer_private_key = priv_key_cls.generate()
        subject_private_key = priv_key_cls.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, None)
        issuer_private_key.public_key().verify(
            cert.signature, cert.tbs_certificate_bytes
        )
        assert cert.signature_algorithm_oid == sig_oid
        assert cert.signature_hash_algorithm is None
        assert cert.signature_algorithm_parameters is None
        assert isinstance(cert.public_key(), pub_key_cls)
        assert cert.public_key_algorithm_oid == pub_oid
        assert cert.version is x509.Version.v3

    @pytest.mark.supported(
        only_if=lambda backend: (
            backend.mldsa_supported() and backend.mlkem_supported()
        ),
        skip_message="Requires a backend with ML-DSA and ML-KEM support",
    )
    @pytest.mark.parametrize(
        (
            "issuer_key_cls",
            "priv_subject_key_cls",
            "pub_subject_key_cls",
            "sig_oid",
            "pub_oid",
        ),
        [
            (
                mldsa.MLDSA44PrivateKey,
                mlkem.MLKEM768PrivateKey,
                mlkem.MLKEM768PublicKey,
                SignatureAlgorithmOID.ML_DSA_44,
                PublicKeyAlgorithmOID.ML_KEM_768,
            ),
            (
                mldsa.MLDSA65PrivateKey,
                mlkem.MLKEM768PrivateKey,
                mlkem.MLKEM768PublicKey,
                SignatureAlgorithmOID.ML_DSA_65,
                PublicKeyAlgorithmOID.ML_KEM_768,
            ),
            (
                mldsa.MLDSA87PrivateKey,
                mlkem.MLKEM768PrivateKey,
                mlkem.MLKEM768PublicKey,
                SignatureAlgorithmOID.ML_DSA_87,
                PublicKeyAlgorithmOID.ML_KEM_768,
            ),
            (
                mldsa.MLDSA44PrivateKey,
                mlkem.MLKEM1024PrivateKey,
                mlkem.MLKEM1024PublicKey,
                SignatureAlgorithmOID.ML_DSA_44,
                PublicKeyAlgorithmOID.ML_KEM_1024,
            ),
            (
                mldsa.MLDSA65PrivateKey,
                mlkem.MLKEM1024PrivateKey,
                mlkem.MLKEM1024PublicKey,
                SignatureAlgorithmOID.ML_DSA_65,
                PublicKeyAlgorithmOID.ML_KEM_1024,
            ),
            (
                mldsa.MLDSA87PrivateKey,
                mlkem.MLKEM1024PrivateKey,
                mlkem.MLKEM1024PublicKey,
                SignatureAlgorithmOID.ML_DSA_87,
                PublicKeyAlgorithmOID.ML_KEM_1024,
            ),
        ],
    )
    def test_build_cert_with_public_mlkem_mldsa_sig(
        self,
        issuer_key_cls,
        priv_subject_key_cls,
        pub_subject_key_cls,
        sig_oid,
        pub_oid,
    ):
        issuer_private_key = issuer_key_cls.generate()
        subject_private_key = priv_subject_key_cls.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                True,
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, None)
        issuer_private_key.public_key().verify(
            cert.signature, cert.tbs_certificate_bytes
        )
        assert cert.signature_algorithm_oid == sig_oid
        assert cert.signature_hash_algorithm is None
        assert cert.signature_algorithm_parameters is None
        assert isinstance(cert.public_key(), pub_subject_key_cls)
        assert cert.public_key_algorithm_oid == pub_oid
        assert cert.version is x509.Version.v3

    @pytest.mark.supported(
        only_if=lambda backend: backend.mldsa_supported(),
        skip_message="Requires a backend with ML-DSA support",
    )
    def test_build_cert_with_public_mldsa_rsa_sig(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = mldsa.MLDSA65PrivateKey.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashes.SHA256())
        assert cert.signature_hash_algorithm is not None
        issuer_private_key.public_key().verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            padding.PKCS1v15(),
            cert.signature_hash_algorithm,
        )
        assert cert.signature_algorithm_oid == (
            SignatureAlgorithmOID.RSA_WITH_SHA256
        )
        assert isinstance(cert.public_key(), mldsa.MLDSA65PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ML_DSA_65

    @pytest.mark.supported(
        only_if=lambda backend: (
            backend.x25519_supported() and backend.x448_supported()
        ),
        skip_message="Requires OpenSSL with x25519 & x448 support",
    )
    @pytest.mark.parametrize(
        ("priv_key_cls", "pub_key_cls", "pub_key_oid"),
        [
            (
                x25519.X25519PrivateKey,
                x25519.X25519PublicKey,
                PublicKeyAlgorithmOID.X25519,
            ),
            (
                x448.X448PrivateKey,
                x448.X448PublicKey,
                PublicKeyAlgorithmOID.X448,
            ),
        ],
    )
    def test_build_cert_with_public_x25519_x448_rsa_sig(
        self,
        rsa_key_2048: rsa.RSAPrivateKey,
        priv_key_cls,
        pub_key_cls,
        pub_key_oid,
    ):
        issuer_private_key = rsa_key_2048
        subject_private_key = priv_key_cls.generate()

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.sign(issuer_private_key, hashes.SHA256())
        assert cert.signature_hash_algorithm is not None
        issuer_private_key.public_key().verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            padding.PKCS1v15(),
            cert.signature_hash_algorithm,
        )
        assert cert.signature_algorithm_oid == (
            SignatureAlgorithmOID.RSA_WITH_SHA256
        )
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA256)
        assert isinstance(cert.public_key(), pub_key_cls)
        assert cert.public_key_algorithm_oid == pub_key_oid

    def test_build_cert_with_rsa_key_too_small(
        self, rsa_key_512: rsa.RSAPrivateKey
    ):
        issuer_private_key = rsa_key_512
        subject_private_key = rsa_key_512

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        with pytest.raises(ValueError):
            builder.sign(issuer_private_key, hashes.SHA512())

    @pytest.mark.parametrize(
        "add_ext",
        [
            x509.SubjectAlternativeName(
                [
                    # These examples exist to verify compatibility with
                    # certificates that have utf8 encoded data in the ia5string
                    x509.DNSName._init_without_validation("a\xedt\xe1s.test"),
                    x509.RFC822Name._init_without_validation(
                        "test@a\xedt\xe1s.test"
                    ),
                    x509.UniformResourceIdentifier._init_without_validation(
                        "http://a\xedt\xe1s.test"
                    ),
                ]
            ),
            x509.CertificatePolicies(
                [
                    x509.PolicyInformation(
                        x509.ObjectIdentifier("2.16.840.1.12345.1.2.3.4.1"),
                        ["http://other.com/cps"],
                    )
                ]
            ),
            x509.CertificatePolicies(
                [
                    x509.PolicyInformation(
                        x509.ObjectIdentifier("2.16.840.1.12345.1.2.3.4.1"),
                        None,
                    )
                ]
            ),
            x509.CertificatePolicies(
                [
                    x509.PolicyInformation(
                        x509.ObjectIdentifier("2.16.840.1.12345.1.2.3.4.1"),
                        [
                            "http://example.com/cps",
                            "http://other.com/cps",
                            x509.UserNotice(
                                x509.NoticeReference("my org", [1, 2, 3, 4]),
                                "thing",
                            ),
                        ],
                    )
                ]
            ),
            x509.CertificatePolicies(
                [
                    x509.PolicyInformation(
                        x509.ObjectIdentifier("2.16.840.1.12345.1.2.3.4.1"),
                        [
                            "http://example.com/cps",
                            x509.UserNotice(
                                x509.NoticeReference(
                                    "UTF8\u2122'", [1, 2, 3, 4]
                                ),
                                "We heart UTF8!\u2122",
                            ),
                        ],
                    )
                ]
            ),
            x509.CertificatePolicies(
                [
                    x509.PolicyInformation(
                        x509.ObjectIdentifier("2.16.840.1.12345.1.2.3.4.1"),
                        [x509.UserNotice(None, "thing")],
                    )
                ]
            ),
            x509.CertificatePolicies(
                [
                    x509.PolicyInformation(
                        x509.ObjectIdentifier("2.16.840.1.12345.1.2.3.4.1"),
                        [
                            x509.UserNotice(
                                x509.NoticeReference("my org", [1, 2, 3, 4]),
                                None,
                            )
                        ],
                    )
                ]
            ),
            x509.IssuerAlternativeName(
                [
                    x509.DNSName("myissuer"),
                    x509.RFC822Name("email@domain.com"),
                ]
            ),
            x509.ExtendedKeyUsage(
                [
                    ExtendedKeyUsageOID.CLIENT_AUTH,
                    ExtendedKeyUsageOID.SERVER_AUTH,
                    ExtendedKeyUsageOID.CODE_SIGNING,
                ]
            ),
            x509.InhibitAnyPolicy(3),
            x509.TLSFeature([x509.TLSFeatureType.status_request]),
            x509.TLSFeature([x509.TLSFeatureType.status_request_v2]),
            x509.TLSFeature(
                [
                    x509.TLSFeatureType.status_request,
                    x509.TLSFeatureType.status_request_v2,
                ]
            ),
            x509.NameConstraints(
                permitted_subtrees=[
                    x509.IPAddress(ipaddress.IPv4Network("192.168.0.0/24")),
                    x509.IPAddress(ipaddress.IPv4Network("192.168.0.0/29")),
                    x509.IPAddress(ipaddress.IPv4Network("127.0.0.1/32")),
                    x509.IPAddress(ipaddress.IPv4Network("8.0.0.0/8")),
                    x509.IPAddress(ipaddress.IPv4Network("0.0.0.0/0")),
                    x509.IPAddress(
                        ipaddress.IPv6Network("FF:0:0:0:0:0:0:0/96")
                    ),
                    x509.IPAddress(
                        ipaddress.IPv6Network("FF:FF:0:0:0:0:0:0/128")
                    ),
                ],
                excluded_subtrees=[x509.DNSName("name.local")],
            ),
            x509.NameConstraints(
                permitted_subtrees=[
                    x509.IPAddress(ipaddress.IPv4Network("0.0.0.0/0")),
                ],
                excluded_subtrees=None,
            ),
            x509.NameConstraints(
                permitted_subtrees=None,
                excluded_subtrees=[x509.DNSName("name.local")],
            ),
            x509.PolicyConstraints(
                require_explicit_policy=None, inhibit_policy_mapping=1
            ),
            x509.PolicyConstraints(
                require_explicit_policy=3, inhibit_policy_mapping=1
            ),
            x509.PolicyConstraints(
                require_explicit_policy=0, inhibit_policy_mapping=None
            ),
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=None,
                        relative_name=x509.RelativeDistinguishedName(
                            [
                                x509.NameAttribute(
                                    NameOID.COMMON_NAME,
                                    "indirect CRL for indirectCRL CA3",
                                ),
                            ]
                        ),
                        reasons=None,
                        crl_issuer=[
                            x509.DirectoryName(
                                x509.Name(
                                    [
                                        x509.NameAttribute(
                                            NameOID.COUNTRY_NAME, "US"
                                        ),
                                        x509.NameAttribute(
                                            NameOID.ORGANIZATION_NAME,
                                            "Test Certificates 2011",
                                        ),
                                        x509.NameAttribute(
                                            NameOID.ORGANIZATIONAL_UNIT_NAME,
                                            "indirectCRL CA3 cRLIssuer",
                                        ),
                                    ]
                                )
                            )
                        ],
                    )
                ]
            ),
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=[
                            x509.DirectoryName(
                                x509.Name(
                                    [
                                        x509.NameAttribute(
                                            NameOID.COUNTRY_NAME, "US"
                                        ),
                                    ]
                                )
                            )
                        ],
                        relative_name=None,
                        reasons=None,
                        crl_issuer=[
                            x509.DirectoryName(
                                x509.Name(
                                    [
                                        x509.NameAttribute(
                                            NameOID.ORGANIZATION_NAME,
                                            "cryptography Testing",
                                        ),
                                    ]
                                )
                            )
                        ],
                    )
                ]
            ),
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=[
                            x509.UniformResourceIdentifier(
                                "http://myhost.com/myca.crl"
                            ),
                            x509.UniformResourceIdentifier(
                                "http://backup.myhost.com/myca.crl"
                            ),
                        ],
                        relative_name=None,
                        reasons=frozenset(
                            [
                                x509.ReasonFlags.key_compromise,
                                x509.ReasonFlags.ca_compromise,
                            ]
                        ),
                        crl_issuer=[
                            x509.DirectoryName(
                                x509.Name(
                                    [
                                        x509.NameAttribute(
                                            NameOID.COUNTRY_NAME, "US"
                                        ),
                                        x509.NameAttribute(
                                            NameOID.COMMON_NAME,
                                            "cryptography CA",
                                        ),
                                    ]
                                )
                            )
                        ],
                    )
                ]
            ),
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=[
                            x509.UniformResourceIdentifier(
                                "http://domain.com/some.crl"
                            )
                        ],
                        relative_name=None,
                        reasons=frozenset(
                            [
                                x509.ReasonFlags.key_compromise,
                                x509.ReasonFlags.ca_compromise,
                                x509.ReasonFlags.affiliation_changed,
                                x509.ReasonFlags.superseded,
                                x509.ReasonFlags.privilege_withdrawn,
                                x509.ReasonFlags.cessation_of_operation,
                                x509.ReasonFlags.aa_compromise,
                                x509.ReasonFlags.certificate_hold,
                            ]
                        ),
                        crl_issuer=None,
                    )
                ]
            ),
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=None,
                        relative_name=None,
                        reasons=None,
                        crl_issuer=[
                            x509.DirectoryName(
                                x509.Name(
                                    [
                                        x509.NameAttribute(
                                            NameOID.COMMON_NAME,
                                            "cryptography CA",
                                        ),
                                    ]
                                )
                            )
                        ],
                    )
                ]
            ),
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=[
                            x509.UniformResourceIdentifier(
                                "http://domain.com/some.crl"
                            )
                        ],
                        relative_name=None,
                        reasons=frozenset([x509.ReasonFlags.aa_compromise]),
                        crl_issuer=None,
                    )
                ]
            ),
            # Regression test: empty frozenset reasons previously panicked
            # in encode_distribution_point_reasons (trailing_zeros(0) == 8).
            x509.CRLDistributionPoints(
                [
                    x509.DistributionPoint(
                        full_name=[
                            x509.UniformResourceIdentifier(
                                "http://crl.example.com/root.crl"
                            )
                        ],
                        relative_name=None,
                        reasons=frozenset(),
                        crl_issuer=None,
                    )
                ]
            ),
            x509.FreshestCRL(
                [
                    x509.DistributionPoint(
                        full_name=[
                            x509.UniformResourceIdentifier(
                                "http://domain.com/some.crl"
                            )
                        ],
                        relative_name=None,
                        reasons=frozenset(
                            [
                                x509.ReasonFlags.key_compromise,
                                x509.ReasonFlags.ca_compromise,
                                x509.ReasonFlags.affiliation_changed,
                                x509.ReasonFlags.superseded,
                                x509.ReasonFlags.privilege_withdrawn,
                                x509.ReasonFlags.cessation_of_operation,
                                x509.ReasonFlags.aa_compromise,
                                x509.ReasonFlags.certificate_hold,
                            ]
                        ),
                        crl_issuer=None,
                    )
                ]
            ),
            x509.FreshestCRL(
                [
                    x509.DistributionPoint(
                        full_name=None,
                        relative_name=x509.RelativeDistinguishedName(
                            [
                                x509.NameAttribute(
                                    NameOID.COMMON_NAME,
                                    "indirect CRL for indirectCRL CA3",
                                ),
                            ]
                        ),
                        reasons=None,
                        crl_issuer=None,
                    )
                ]
            ),
            x509.FreshestCRL(
                [
                    x509.DistributionPoint(
                        full_name=None,
                        relative_name=x509.RelativeDistinguishedName(
                            [
                                x509.NameAttribute(
                                    NameOID.COMMON_NAME,
                                    "indirect CRL for indirectCRL CA3",
                                ),
                                x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                            ]
                        ),
                        reasons=None,
                        crl_issuer=None,
                    )
                ]
            ),
            x509.AuthorityInformationAccess(
                [
                    x509.AccessDescription(
                        AuthorityInformationAccessOID.OCSP,
                        x509.UniformResourceIdentifier(
                            "http://ocsp.domain.com"
                        ),
                    ),
                    x509.AccessDescription(
                        AuthorityInformationAccessOID.CA_ISSUERS,
                        x509.UniformResourceIdentifier(
                            "http://domain.com/ca.crt"
                        ),
                    ),
                ]
            ),
            x509.SubjectInformationAccess(
                [
                    x509.AccessDescription(
                        SubjectInformationAccessOID.CA_REPOSITORY,
                        x509.UniformResourceIdentifier("http://ca.domain.com"),
                    ),
                ]
            ),
            x509.AuthorityKeyIdentifier(
                b"\xc3\x9c\xf3\xfc\xd3F\x084\xbb\xceF\x7f\xa0|[\xf3\xe2\x08"
                b"\xcbY",
                None,
                None,
            ),
            x509.AuthorityKeyIdentifier(
                b"\xc3\x9c\xf3\xfc\xd3F\x084\xbb\xceF\x7f\xa0|[\xf3\xe2\x08"
                b"\xcbY",
                [
                    x509.DirectoryName(
                        x509.Name(
                            [
                                x509.NameAttribute(
                                    NameOID.ORGANIZATION_NAME, "PyCA"
                                ),
                                x509.NameAttribute(
                                    NameOID.COMMON_NAME, "cryptography CA"
                                ),
                            ]
                        )
                    )
                ],
                333,
            ),
            x509.AuthorityKeyIdentifier(
                None,
                [
                    x509.DirectoryName(
                        x509.Name(
                            [
                                x509.NameAttribute(
                                    NameOID.ORGANIZATION_NAME, "PyCA"
                                ),
                                x509.NameAttribute(
                                    NameOID.COMMON_NAME, "cryptography CA"
                                ),
                            ]
                        )
                    )
                ],
                333,
            ),
            x509.KeyUsage(
                digital_signature=True,
                content_commitment=True,
                key_encipherment=False,
                data_encipherment=False,
                key_agreement=False,
                key_cert_sign=True,
                crl_sign=False,
                encipher_only=False,
                decipher_only=False,
            ),
            x509.PrivateKeyUsagePeriod(
                not_before=datetime.datetime(2002, 1, 1, 12, 1),
                not_after=datetime.datetime(2030, 12, 31, 8, 30),
            ),
            x509.OCSPNoCheck(),
            x509.SubjectKeyIdentifier,
        ],
    )
    def test_extensions(self, rsa_key_2048: rsa.RSAPrivateKey, add_ext):
        issuer_private_key = rsa_key_2048
        subject_private_key = rsa_key_2048

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        if add_ext is x509.SubjectKeyIdentifier:
            add_ext = x509.SubjectKeyIdentifier.from_public_key(
                subject_private_key.public_key()
            )

        # Cert
        cert = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
            .public_key(subject_private_key.public_key())
            .serial_number(123)
            .add_extension(add_ext, critical=False)
            .sign(issuer_private_key, hashes.SHA256())
        )

        ext = cert.extensions.get_extension_for_class(type(add_ext))
        assert ext.critical is False
        assert ext.value == add_ext

        # CSR
        csr = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .add_extension(add_ext, False)
            .sign(subject_private_key, hashes.SHA256())
        )
        ext = csr.extensions.get_extension_for_class(type(add_ext))
        assert ext.critical is False
        assert ext.value == add_ext

    def test_build_ca_request_with_path_length_none(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA")]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=None), critical=True
            )
            .sign(private_key, hashes.SHA256())
        )

        loaded_request = x509.load_pem_x509_csr(
            request.public_bytes(encoding=serialization.Encoding.PEM)
        )
        subject = loaded_request.subject
        assert isinstance(subject, x509.Name)
        basic_constraints = request.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.path_length is None

    @pytest.mark.parametrize(
        "unrecognized",
        [
            x509.UnrecognizedExtension(
                x509.ObjectIdentifier("1.2.3.4.5"),
                b"abcdef",
            )
        ],
    )
    def test_unrecognized_extension(
        self, rsa_key_2048: rsa.RSAPrivateKey, unrecognized
    ):
        private_key = rsa_key_2048

        cert = (
            x509.CertificateBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(x509.OID_COUNTRY_NAME, "US")])
            )
            .issuer_name(
                x509.Name([x509.NameAttribute(x509.OID_COUNTRY_NAME, "US")])
            )
            .not_valid_before(datetime.datetime(2002, 1, 1, 12, 1))
            .not_valid_after(datetime.datetime(2030, 12, 31, 8, 30))
            .public_key(private_key.public_key())
            .serial_number(123)
            .add_extension(unrecognized, critical=False)
            .sign(private_key, hashes.SHA256())
        )

        ext = cert.extensions.get_extension_for_oid(unrecognized.oid)

        assert ext.value == unrecognized

    def test_sign_without_private_key(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "NO")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "NO")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        with pytest.raises(TypeError):
            builder.sign(None, None)  # type:ignore[arg-type]

    def test_build_unsigned_cert(self, rsa_key_2048: rsa.RSAPrivateKey):
        subject_private_key = rsa_key_2048

        not_valid_before = datetime.datetime(2002, 1, 1, 12, 1)
        not_valid_after = datetime.datetime(2030, 12, 31, 8, 30)

        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "NO")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "NO")])
            )
            .public_key(subject_private_key.public_key())
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        cert = builder.create_unsigned()

        assert cert.public_key() == subject_private_key.public_key()
        assert cert.signature_algorithm_oid == SignatureAlgorithmOID.UNSIGNED
        assert cert.signature_hash_algorithm is None
        assert cert.signature_algorithm_parameters is None
        assert cert.signature == b""

        with pytest.raises(
            ValueError, match="Unsupported signature algorithm"
        ):
            cert.verify_directly_issued_by(cert)


class TestCertificateSigningRequestBuilder:
    def test_sign_invalid_hash_algorithm(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048

        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([])
        )
        with pytest.raises(TypeError):
            builder.sign(private_key, typing.cast(typing.Any, "NotAHash"))

    def test_request_with_unsupported_hash_ed25519(self):
        private_key = ed25519.Ed25519PrivateKey.generate()
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    @pytest.mark.supported(
        only_if=lambda backend: backend.ed448_supported(),
        skip_message="Requires OpenSSL with Ed448 support",
    )
    def test_request_with_unsupported_hash_ed448(self):
        private_key = ed448.Ed448PrivateKey.generate()
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    def test_no_subject_name(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        builder = x509.CertificateSigningRequestBuilder()
        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    def test_build_ca_request_with_rsa(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA")]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, hashes.SHA256())
        )

        assert isinstance(request.signature_hash_algorithm, hashes.SHA256)
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
        ]
        basic_constraints = request.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2

    def test_build_ca_request_with_unicode(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.ORGANIZATION_NAME, "PyCA\U0001f37a"
                        ),
                    ]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, hashes.SHA256())
        )

        loaded_request = x509.load_pem_x509_csr(
            request.public_bytes(encoding=serialization.Encoding.PEM)
        )
        subject = loaded_request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA\U0001f37a"),
        ]

    def test_subject_dn_asn1_types(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(NameOID.COMMON_NAME, "mysite.com"),
                        x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                        x509.NameAttribute(NameOID.LOCALITY_NAME, "value"),
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "value"
                        ),
                        x509.NameAttribute(NameOID.STREET_ADDRESS, "value"),
                        x509.NameAttribute(NameOID.ORGANIZATION_NAME, "value"),
                        x509.NameAttribute(
                            NameOID.ORGANIZATIONAL_UNIT_NAME, "value"
                        ),
                        x509.NameAttribute(NameOID.SERIAL_NUMBER, "value"),
                        x509.NameAttribute(NameOID.SURNAME, "value"),
                        x509.NameAttribute(NameOID.GIVEN_NAME, "value"),
                        x509.NameAttribute(NameOID.TITLE, "value"),
                        x509.NameAttribute(
                            NameOID.GENERATION_QUALIFIER, "value"
                        ),
                        x509.NameAttribute(
                            NameOID.X500_UNIQUE_IDENTIFIER, "value"
                        ),
                        x509.NameAttribute(NameOID.DN_QUALIFIER, "value"),
                        x509.NameAttribute(NameOID.PSEUDONYM, "value"),
                        x509.NameAttribute(NameOID.USER_ID, "value"),
                        x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "value"),
                        x509.NameAttribute(NameOID.EMAIL_ADDRESS, "value"),
                        x509.NameAttribute(
                            NameOID.JURISDICTION_COUNTRY_NAME, "US"
                        ),
                        x509.NameAttribute(
                            NameOID.JURISDICTION_LOCALITY_NAME, "value"
                        ),
                        x509.NameAttribute(
                            NameOID.JURISDICTION_STATE_OR_PROVINCE_NAME,
                            "value",
                        ),
                        x509.NameAttribute(NameOID.BUSINESS_CATEGORY, "value"),
                        x509.NameAttribute(NameOID.POSTAL_ADDRESS, "value"),
                        x509.NameAttribute(NameOID.POSTAL_CODE, "value"),
                    ]
                )
            )
            .sign(private_key, hashes.SHA256())
        )
        for oid, asn1_type in TestNameAttribute.EXPECTED_TYPES:
            assert (
                request.subject.get_attributes_for_oid(oid)[0]._type
                == asn1_type
            )

    def test_build_ca_request_with_multivalue_rdns(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048
        subject = x509.Name(
            [
                x509.RelativeDistinguishedName(
                    [
                        x509.NameAttribute(NameOID.TITLE, "Test"),
                        x509.NameAttribute(NameOID.COMMON_NAME, "Multivalue"),
                        x509.NameAttribute(NameOID.SURNAME, "RDNs"),
                    ]
                ),
                x509.RelativeDistinguishedName(
                    [x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA")]
                ),
            ]
        )

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(subject)
            .sign(private_key, hashes.SHA256())
        )

        loaded_request = x509.load_pem_x509_csr(
            request.public_bytes(encoding=serialization.Encoding.PEM)
        )
        assert isinstance(loaded_request.subject, x509.Name)
        assert loaded_request.subject == subject

    def test_build_nonca_request_with_rsa(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .add_extension(
                x509.BasicConstraints(ca=False, path_length=None),
                critical=True,
            )
            .sign(private_key, hashes.SHA256())
        )

        assert isinstance(request.signature_hash_algorithm, hashes.SHA256)
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
        ]
        basic_constraints = request.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is False
        assert basic_constraints.value.path_length is None

    def test_build_ca_request_with_ec(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        private_key = ec.generate_private_key(ec.SECP256R1(), backend)

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, hashes.SHA256(), backend)
        )

        assert isinstance(request.signature_hash_algorithm, hashes.SHA256)
        public_key = request.public_key()
        assert isinstance(public_key, ec.EllipticCurvePublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
        ]
        basic_constraints = request.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2

    def test_build_ca_request_with_deterministic_ec(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        _skip_deterministic_ecdsa_unsupported(backend)

        private_key = ec.generate_private_key(ec.SECP256R1())

        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([])
        )
        csr1 = builder.sign(
            private_key,
            hashes.SHA256(),
            backend,
            ecdsa_deterministic=True,
        )
        csr2 = builder.sign(
            private_key,
            hashes.SHA256(),
            backend,
            ecdsa_deterministic=True,
        )

        csr_nondet = builder.sign(
            private_key,
            hashes.SHA256(),
            backend,
        )

        csr_nondet2 = builder.sign(
            private_key,
            hashes.SHA256(),
            backend,
        )

        assert csr1.signature == csr2.signature
        assert csr1.signature != csr_nondet.signature
        assert csr_nondet.signature != csr_nondet2.signature
        private_key.public_key().verify(
            csr1.signature,
            csr1.tbs_certrequest_bytes,
            ec.ECDSA(hashes.SHA256()),
        )

    def test_csr_deterministic_wrong_key_type(self, rsa_key_2048):
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([])
        )
        with pytest.raises(TypeError):
            builder.sign(
                rsa_key_2048, hashes.SHA256(), ecdsa_deterministic=True
            )

    def test_build_ca_request_with_ed25519(self):
        private_key = ed25519.Ed25519PrivateKey.generate()

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, None)
        )

        assert request.signature_hash_algorithm is None
        public_key = request.public_key()
        assert isinstance(public_key, ed25519.Ed25519PublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
        ]
        basic_constraints = request.extensions.get_extension_for_class(
            x509.BasicConstraints
        )
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2

    @pytest.mark.supported(
        only_if=lambda backend: backend.ed448_supported(),
        skip_message="Requires OpenSSL with Ed448 support",
    )
    def test_build_ca_request_with_ed448(self):
        private_key = ed448.Ed448PrivateKey.generate()

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, None)
        )

        assert request.signature_hash_algorithm is None
        public_key = request.public_key()
        assert isinstance(public_key, ed448.Ed448PublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
        ]
        basic_constraints = request.extensions.get_extension_for_class(
            x509.BasicConstraints
        )
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2

    @pytest.mark.supported(
        only_if=lambda backend: backend.mldsa_supported(),
        skip_message="Requires a backend with ML-DSA support",
    )
    @pytest.mark.parametrize(
        ("priv_key_cls", "pub_key_cls", "sig_oid"),
        [
            (
                mldsa.MLDSA44PrivateKey,
                mldsa.MLDSA44PublicKey,
                SignatureAlgorithmOID.ML_DSA_44,
            ),
            (
                mldsa.MLDSA65PrivateKey,
                mldsa.MLDSA65PublicKey,
                SignatureAlgorithmOID.ML_DSA_65,
            ),
            (
                mldsa.MLDSA87PrivateKey,
                mldsa.MLDSA87PublicKey,
                SignatureAlgorithmOID.ML_DSA_87,
            ),
        ],
    )
    def test_build_ca_request_with_mldsa(
        self, priv_key_cls, pub_key_cls, sig_oid
    ):
        private_key = priv_key_cls.generate()

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, None)
        )

        assert request.is_signature_valid
        assert request.signature_algorithm_oid == sig_oid
        assert request.signature_hash_algorithm is None
        public_key = request.public_key()
        assert isinstance(public_key, pub_key_cls)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
        ]
        basic_constraints = request.extensions.get_extension_for_class(
            x509.BasicConstraints
        )
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2

    @pytest.mark.supported(
        only_if=lambda backend: backend.dsa_supported(),
        skip_message="Does not support DSA.",
    )
    def test_build_ca_request_with_dsa(self):
        private_key = DSA_KEY_2048.private_key()

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, hashes.SHA256())
        )

        assert isinstance(request.signature_hash_algorithm, hashes.SHA256)
        public_key = request.public_key()
        assert isinstance(public_key, dsa.DSAPublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
        ]
        basic_constraints = request.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2

    def test_add_duplicate_extension(self):
        builder = x509.CertificateSigningRequestBuilder().add_extension(
            x509.BasicConstraints(True, 2),
            critical=True,
        )
        with pytest.raises(ValueError):
            builder.add_extension(
                x509.BasicConstraints(True, 2),
                critical=True,
            )

    def test_set_invalid_subject(self):
        builder = x509.CertificateSigningRequestBuilder()
        with pytest.raises(TypeError):
            builder.subject_name(typing.cast(typing.Any, "NotAName"))

    def test_add_invalid_extension_type(self):
        builder = x509.CertificateSigningRequestBuilder()

        with pytest.raises(TypeError):
            builder.add_extension(
                typing.cast(typing.Any, object()),
                False,
            )

    def test_add_unsupported_extension(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048
        builder = x509.CertificateSigningRequestBuilder()
        builder = (
            builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .add_extension(DummyExtension(), False)
        )
        with pytest.raises(NotImplementedError):
            builder.sign(private_key, hashes.SHA256())

    def test_add_two_extensions(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048
        builder = x509.CertificateSigningRequestBuilder()
        request = (
            builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .add_extension(
                x509.SubjectAlternativeName([x509.DNSName("cryptography.io")]),
                critical=False,
            )
            .add_extension(
                x509.BasicConstraints(ca=True, path_length=2), critical=True
            )
            .sign(private_key, hashes.SHA256())
        )

        assert isinstance(request.signature_hash_algorithm, hashes.SHA256)
        public_key = request.public_key()
        assert isinstance(public_key, rsa.RSAPublicKey)
        basic_constraints = request.extensions.get_extension_for_oid(
            ExtensionOID.BASIC_CONSTRAINTS
        )
        assert isinstance(basic_constraints.value, x509.BasicConstraints)
        assert basic_constraints.value.ca is True
        assert basic_constraints.value.path_length == 2
        ext = request.extensions.get_extension_for_oid(
            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
        )
        assert isinstance(ext.value, x509.SubjectAlternativeName)
        assert list(ext.value) == [x509.DNSName("cryptography.io")]

    def test_add_attributes(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        private_key = ec.generate_private_key(ec.SECP256R1(), backend)
        challenge_password = b"challenge me!"
        unstructured_name = b"no structure, for shame"
        locality = b"this shouldn't even be an X509 attribute"

        request = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name(
                    [
                        x509.NameAttribute(
                            NameOID.STATE_OR_PROVINCE_NAME, "Texas"
                        ),
                    ]
                )
            )
            .add_attribute(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD, challenge_password
            )
            .add_attribute(
                x509.oid.AttributeOID.UNSTRUCTURED_NAME, unstructured_name
            )
            .add_attribute(x509.oid.NameOID.LOCALITY_NAME, locality)
            .add_extension(
                x509.ExtendedKeyUsage(
                    [
                        ExtendedKeyUsageOID.CLIENT_AUTH,
                        ExtendedKeyUsageOID.SERVER_AUTH,
                        ExtendedKeyUsageOID.CODE_SIGNING,
                    ]
                ),
                False,
            )
            .sign(private_key, hashes.SHA256(), backend)
        )

        assert (
            request.attributes.get_attribute_for_oid(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD
            ).value
            == challenge_password
        )
        assert (
            request.attributes.get_attribute_for_oid(
                x509.oid.AttributeOID.UNSTRUCTURED_NAME
            ).value
            == unstructured_name
        )
        assert (
            request.attributes.get_attribute_for_oid(
                x509.oid.NameOID.LOCALITY_NAME
            ).value
            == locality
        )
        assert len(request.attributes) == 4

    def test_add_attributes_non_utf8(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        private_key = ec.generate_private_key(ec.SECP256R1(), backend)
        builder = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(x509.Name([]))
            .add_attribute(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD,
                b"\xbb\xad\x16\x9a\xac\xc9\x03i\xec\xcc\xdd6\xcbh\xfc\xf3",
            )
        )
        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256(), backend)

    def test_add_attribute_bad_types(self):
        request = x509.CertificateSigningRequestBuilder()
        with pytest.raises(TypeError):
            request.add_attribute(
                typing.cast(typing.Any, b"not an oid"),
                b"val",
            )

        with pytest.raises(TypeError):
            request.add_attribute(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD,
                typing.cast(typing.Any, 383),
            )

    def test_duplicate_attribute(self):
        request = x509.CertificateSigningRequestBuilder().add_attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD, b"val"
        )
        with pytest.raises(ValueError):
            request.add_attribute(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD, b"val2"
            )

    def test_add_attribute_tag(self):
        private_key = ec.generate_private_key(ec.SECP256R1())
        builder = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(x509.Name([]))
            .add_attribute(
                x509.ObjectIdentifier("1.2.3.4"),
                b"\x00\x00",
                _tag=_ASN1Type.GeneralizedTime,
            )
        )
        request = builder.sign(private_key, hashes.SHA256())
        attr = request.attributes.get_attribute_for_oid(
            x509.ObjectIdentifier("1.2.3.4")
        )

        assert attr.value == b"\x00\x00"
        assert attr._type == _ASN1Type.GeneralizedTime.value

    def test_add_attribute_tag_non_int(self):
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([])
        )
        with pytest.raises(TypeError):
            builder.add_attribute(
                x509.ObjectIdentifier("1.2.3.4"),
                b"",
                _tag=typing.cast(typing.Any, object()),
            )

    def test_set_subject_twice(self):
        builder = x509.CertificateSigningRequestBuilder()
        builder = builder.subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )
        with pytest.raises(ValueError):
            builder.subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )

    @pytest.mark.parametrize(
        "add_ext",
        [
            x509.KeyUsage(
                digital_signature=True,
                content_commitment=True,
                key_encipherment=False,
                data_encipherment=False,
                key_agreement=False,
                key_cert_sign=True,
                crl_sign=False,
                encipher_only=False,
                decipher_only=False,
            ),
            x509.KeyUsage(
                digital_signature=False,
                content_commitment=False,
                key_encipherment=False,
                data_encipherment=False,
                key_agreement=True,
                key_cert_sign=True,
                crl_sign=False,
                encipher_only=False,
                decipher_only=True,
            ),
            x509.SubjectAlternativeName(
                [
                    x509.DNSName("example.com"),
                    x509.DNSName("*.example.com"),
                    x509.RegisteredID(x509.ObjectIdentifier("1.2.3.4.5.6.7")),
                    x509.DirectoryName(
                        x509.Name(
                            [
                                x509.NameAttribute(
                                    NameOID.COMMON_NAME, "PyCA"
                                ),
                                x509.NameAttribute(
                                    NameOID.ORGANIZATION_NAME,
                                    "We heart UTF8!\u2122",
                                ),
                            ]
                        )
                    ),
                    x509.IPAddress(ipaddress.ip_address("127.0.0.1")),
                    x509.IPAddress(ipaddress.ip_address("ff::")),
                    x509.OtherName(
                        type_id=x509.ObjectIdentifier("1.2.3.3.3.3"),
                        value=b"0\x03\x02\x01\x05",
                    ),
                    x509.RFC822Name("test@example.com"),
                    x509.RFC822Name("email"),
                    x509.RFC822Name("email@xn--eml-vla4c.com"),
                    x509.UniformResourceIdentifier(
                        "https://xn--80ato2c.cryptography"
                    ),
                    x509.UniformResourceIdentifier(
                        "gopher://cryptography:70/some/path"
                    ),
                ]
            ),
            x509.ExtendedKeyUsage(
                [
                    ExtendedKeyUsageOID.CLIENT_AUTH,
                    ExtendedKeyUsageOID.SERVER_AUTH,
                    ExtendedKeyUsageOID.CODE_SIGNING,
                ]
            ),
        ],
    )
    def test_extensions(self, rsa_key_2048: rsa.RSAPrivateKey, add_ext):
        private_key = rsa_key_2048

        csr = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "SAN")])
            )
            .add_extension(
                add_ext,
                critical=False,
            )
            .sign(private_key, hashes.SHA256())
        )

        assert len(csr.extensions) == 1
        ext = csr.extensions.get_extension_for_class(type(add_ext))
        assert not ext.critical
        assert ext.value == add_ext

    def test_invalid_asn1_othername(self, rsa_key_2048: rsa.RSAPrivateKey):
        private_key = rsa_key_2048

        builder = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "SAN")])
            )
            .add_extension(
                x509.SubjectAlternativeName(
                    [
                        x509.OtherName(
                            type_id=x509.ObjectIdentifier("1.2.3.3.3.3"),
                            # Invalid length
                            value=b"\x01\x05\x01\x05",
                        ),
                    ]
                ),
                critical=False,
            )
        )
        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    def test_subject_alt_name_unsupported_general_name(
        self, rsa_key_2048: rsa.RSAPrivateKey
    ):
        private_key = rsa_key_2048

        builder = (
            x509.CertificateSigningRequestBuilder()
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "SAN")])
            )
            .add_extension(
                x509.SubjectAlternativeName([FakeGeneralName("")]),
                critical=False,
            )
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA256())

    def test_rsa_key_too_small(self, rsa_key_512: rsa.RSAPrivateKey):
        private_key = rsa_key_512
        builder = x509.CertificateSigningRequestBuilder()
        builder = builder.subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )

        with pytest.raises(ValueError):
            builder.sign(private_key, hashes.SHA512())

    @pytest.mark.parametrize(
        ("alg", "mgf_alg"),
        [
            (hashes.SHA512(), hashes.SHA256()),
            (hashes.SHA3_512(), hashes.SHA3_256()),
        ],
    )
    def test_sign_pss(
        self, rsa_key_2048: rsa.RSAPrivateKey, alg, mgf_alg, backend
    ):
        if not backend.signature_hash_supported(alg):
            pytest.skip(f"{alg} signature not supported")
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )
        pss = padding.PSS(
            mgf=padding.MGF1(mgf_alg), salt_length=alg.digest_size
        )
        csr = builder.sign(rsa_key_2048, alg, rsa_padding=pss)
        pk = csr.public_key()
        assert isinstance(pk, rsa.RSAPublicKey)
        assert isinstance(csr.signature_hash_algorithm, type(alg))
        cert_params = csr.signature_algorithm_parameters
        assert isinstance(cert_params, padding.PSS)
        assert cert_params._salt_length == pss._salt_length
        assert isinstance(cert_params._mgf, padding.MGF1)
        assert isinstance(cert_params._mgf._algorithm, type(mgf_alg))
        pk.verify(
            csr.signature,
            csr.tbs_certrequest_bytes,
            cert_params,
            alg,
        )

    @pytest.mark.parametrize(
        ("padding_len", "computed_len"),
        [
            (padding.PSS.MAX_LENGTH, 222),
            (padding.PSS.DIGEST_LENGTH, 32),
        ],
    )
    def test_sign_pss_length_options(
        self,
        rsa_key_2048: rsa.RSAPrivateKey,
        padding_len,
        computed_len,
        backend,
    ):
        pss = padding.PSS(
            mgf=padding.MGF1(hashes.SHA256()), salt_length=padding_len
        )
        if not backend.rsa_padding_supported(pss):
            pytest.skip("PSS padding with these parameters not supported")

        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )
        pss = padding.PSS(
            mgf=padding.MGF1(hashes.SHA256()), salt_length=padding_len
        )
        csr = builder.sign(rsa_key_2048, hashes.SHA256(), rsa_padding=pss)
        assert isinstance(csr.signature_algorithm_parameters, padding.PSS)
        assert csr.signature_algorithm_parameters._salt_length == computed_len

    def test_sign_pss_auto_unsupported(self, rsa_key_2048: rsa.RSAPrivateKey):
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )
        pss = padding.PSS(
            mgf=padding.MGF1(hashes.SHA256()), salt_length=padding.PSS.AUTO
        )
        with pytest.raises(TypeError):
            builder.sign(rsa_key_2048, hashes.SHA256(), rsa_padding=pss)

    def test_sign_invalid_padding(self, rsa_key_2048: rsa.RSAPrivateKey):
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )
        with pytest.raises(TypeError):
            builder.sign(
                rsa_key_2048,
                hashes.SHA256(),
                rsa_padding=typing.cast(typing.Any, b"notapadding"),
            )
        eckey = ec.generate_private_key(ec.SECP256R1())
        with pytest.raises(TypeError):
            builder.sign(
                eckey, hashes.SHA256(), rsa_padding=padding.PKCS1v15()
            )

    def test_sign_pss_hash_none(self, rsa_key_2048: rsa.RSAPrivateKey):
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )
        pss = padding.PSS(mgf=padding.MGF1(hashes.SHA256()), salt_length=32)
        with pytest.raises(TypeError):
            builder.sign(rsa_key_2048, None, rsa_padding=pss)


@pytest.mark.supported(
    only_if=lambda backend: backend.dsa_supported(),
    skip_message="Does not support DSA.",
)
class TestDSACertificate:
    @pytest.mark.supported(
        only_if=lambda backend: backend.signature_hash_supported(
            hashes.SHA1()
        ),
        skip_message="Does not support SHA-1 signature.",
    )
    def test_load_dsa_cert(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "dsa_selfsigned_ca.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA1)
        public_key = cert.public_key()
        assert isinstance(public_key, dsa.DSAPublicKey)
        assert cert.signature_algorithm_parameters is None
        num = public_key.public_numbers()
        assert num.y == int(
            "4c08bfe5f2d76649c80acf7d431f6ae2124b217abc8c9f6aca776ddfa94"
            "53b6656f13e543684cd5f6431a314377d2abfa068b7080cb8ddc065afc2"
            "dea559f0b584c97a2b235b9b69b46bc6de1aed422a6f341832618bcaae2"
            "198aba388099dafb05ff0b5efecb3b0ae169a62e1c72022af50ae68af3b"
            "033c18e6eec1f7df4692c456ccafb79cc7e08da0a5786e9816ceda651d6"
            "1b4bb7b81c2783da97cea62df67af5e85991fdc13aff10fc60e06586386"
            "b96bb78d65750f542f86951e05a6d81baadbcd35a2e5cad4119923ae6a2"
            "002091a3d17017f93c52970113cdc119970b9074ca506eac91c3dd37632"
            "5df4af6b3911ef267d26623a5a1c5df4a6d13f1c",
            16,
        )
        assert num.parameter_numbers.g == int(
            "4b7ced71dc353965ecc10d441a9a06fc24943a32d66429dd5ef44d43e67"
            "d789d99770aec32c0415dc92970880872da45fef8dd1e115a3e4801387b"
            "a6d755861f062fd3b6e9ea8e2641152339b828315b1528ee6c7b79458d2"
            "1f3db973f6fc303f9397174c2799dd2351282aa2d8842c357a73495bbaa"
            "c4932786414c55e60d73169f5761036fba29e9eebfb049f8a3b1b7cee6f"
            "3fbfa136205f130bee2cf5b9c38dc1095d4006f2e73335c07352c64130a"
            "1ab2b89f13b48f628d3cc3868beece9bb7beade9f830eacc6fa241425c0"
            "b3fcc0df416a0c89f7bf35668d765ec95cdcfbe9caff49cfc156c668c76"
            "fa6247676a6d3ac945844a083509c6a1b436baca",
            16,
        )
        assert num.parameter_numbers.p == int(
            "bfade6048e373cd4e48b677e878c8e5b08c02102ae04eb2cb5c46a523a3"
            "af1c73d16b24f34a4964781ae7e50500e21777754a670bd19a7420d6330"
            "84e5556e33ca2c0e7d547ea5f46a07a01bf8669ae3bdec042d9b2ae5e6e"
            "cf49f00ba9dac99ab6eff140d2cedf722ee62c2f9736857971444c25d0a"
            "33d2017dc36d682a1054fe2a9428dda355a851ce6e6d61e03e419fd4ca4"
            "e703313743d86caa885930f62ed5bf342d8165627681e9cc3244ba72aa2"
            "2148400a6bbe80154e855d042c9dc2a3405f1e517be9dea50562f56da93"
            "f6085f844a7e705c1f043e65751c583b80d29103e590ccb26efdaa0893d"
            "833e36468f3907cfca788a3cb790f0341c8a31bf",
            16,
        )
        assert num.parameter_numbers.q == int(
            "822ff5d234e073b901cf5941f58e1f538e71d40d", 16
        )

    def test_load_dsa_cert_null_alg_params(self):
        """
        This test verifies that we reject certificates with encoded null
        parameters in the DSA signature AlgorithmIdentifier. This is invalid;
        Java versions less than 21 generated certificates with this encoding,
        but we no longer tolerate it.
        """
        with pytest.raises(ValueError):
            _load_cert(
                os.path.join("x509", "custom", "dsa_null_alg_params.pem"),
                x509.load_pem_x509_certificate,
            )

    def test_signature(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "dsa_selfsigned_ca.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.signature == binascii.unhexlify(
            b"302c021425c4a84a936ab311ee017d3cbd9a3c650bb3ae4a02145d30c64b4326"
            b"86bdf925716b4ed059184396bcce"
        )
        r, s = decode_dss_signature(cert.signature)
        assert r == 215618264820276283222494627481362273536404860490
        assert s == 532023851299196869156027211159466197586787351758

    def test_tbs_certificate_bytes(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "dsa_selfsigned_ca.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.tbs_certificate_bytes == binascii.unhexlify(
            b"3082051aa003020102020900a37352e0b2142f86300906072a8648ce3804033"
            b"067310b3009060355040613025553310e300c06035504081305546578617331"
            b"0f300d0603550407130641757374696e3121301f060355040a1318496e74657"
            b"26e6574205769646769747320507479204c7464311430120603550403130b50"
            b"79434120445341204341301e170d3134313132373035313431375a170d31343"
            b"13232373035313431375a3067310b3009060355040613025553310e300c0603"
            b"55040813055465786173310f300d0603550407130641757374696e3121301f0"
            b"60355040a1318496e7465726e6574205769646769747320507479204c746431"
            b"1430120603550403130b50794341204453412043413082033a3082022d06072"
            b"a8648ce380401308202200282010100bfade6048e373cd4e48b677e878c8e5b"
            b"08c02102ae04eb2cb5c46a523a3af1c73d16b24f34a4964781ae7e50500e217"
            b"77754a670bd19a7420d633084e5556e33ca2c0e7d547ea5f46a07a01bf8669a"
            b"e3bdec042d9b2ae5e6ecf49f00ba9dac99ab6eff140d2cedf722ee62c2f9736"
            b"857971444c25d0a33d2017dc36d682a1054fe2a9428dda355a851ce6e6d61e0"
            b"3e419fd4ca4e703313743d86caa885930f62ed5bf342d8165627681e9cc3244"
            b"ba72aa22148400a6bbe80154e855d042c9dc2a3405f1e517be9dea50562f56d"
            b"a93f6085f844a7e705c1f043e65751c583b80d29103e590ccb26efdaa0893d8"
            b"33e36468f3907cfca788a3cb790f0341c8a31bf021500822ff5d234e073b901"
            b"cf5941f58e1f538e71d40d028201004b7ced71dc353965ecc10d441a9a06fc2"
            b"4943a32d66429dd5ef44d43e67d789d99770aec32c0415dc92970880872da45"
            b"fef8dd1e115a3e4801387ba6d755861f062fd3b6e9ea8e2641152339b828315"
            b"b1528ee6c7b79458d21f3db973f6fc303f9397174c2799dd2351282aa2d8842"
            b"c357a73495bbaac4932786414c55e60d73169f5761036fba29e9eebfb049f8a"
            b"3b1b7cee6f3fbfa136205f130bee2cf5b9c38dc1095d4006f2e73335c07352c"
            b"64130a1ab2b89f13b48f628d3cc3868beece9bb7beade9f830eacc6fa241425"
            b"c0b3fcc0df416a0c89f7bf35668d765ec95cdcfbe9caff49cfc156c668c76fa"
            b"6247676a6d3ac945844a083509c6a1b436baca0382010500028201004c08bfe"
            b"5f2d76649c80acf7d431f6ae2124b217abc8c9f6aca776ddfa9453b6656f13e"
            b"543684cd5f6431a314377d2abfa068b7080cb8ddc065afc2dea559f0b584c97"
            b"a2b235b9b69b46bc6de1aed422a6f341832618bcaae2198aba388099dafb05f"
            b"f0b5efecb3b0ae169a62e1c72022af50ae68af3b033c18e6eec1f7df4692c45"
            b"6ccafb79cc7e08da0a5786e9816ceda651d61b4bb7b81c2783da97cea62df67"
            b"af5e85991fdc13aff10fc60e06586386b96bb78d65750f542f86951e05a6d81"
            b"baadbcd35a2e5cad4119923ae6a2002091a3d17017f93c52970113cdc119970"
            b"b9074ca506eac91c3dd376325df4af6b3911ef267d26623a5a1c5df4a6d13f1"
            b"ca381cc3081c9301d0603551d0e04160414a4fb887a13fcdeb303bbae9a1dec"
            b"a72f125a541b3081990603551d2304819130818e8014a4fb887a13fcdeb303b"
            b"bae9a1deca72f125a541ba16ba4693067310b3009060355040613025553310e"
            b"300c060355040813055465786173310f300d0603550407130641757374696e3"
            b"121301f060355040a1318496e7465726e657420576964676974732050747920"
            b"4c7464311430120603550403130b5079434120445341204341820900a37352e"
            b"0b2142f86300c0603551d13040530030101ff"
        )
        assert cert.signature_hash_algorithm is not None
        public_key = cert.public_key()
        assert isinstance(public_key, dsa.DSAPublicKey)
        public_key.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            cert.signature_hash_algorithm,
        )

    def test_verify_directly_issued_by_dsa(self):
        issuer_private_key = DSA_KEY_3072.private_key()
        subject_private_key = DSA_KEY_2048.private_key()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_dsa_bad_sig(self):
        issuer_private_key = DSA_KEY_3072.private_key()
        subject_private_key = DSA_KEY_2048.private_key()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert_bad_sig = _break_cert_sig(cert)
        with pytest.raises(InvalidSignature):
            cert_bad_sig.verify_directly_issued_by(ca)


@pytest.mark.supported(
    only_if=lambda backend: backend.dsa_supported(),
    skip_message="Does not support DSA.",
)
@pytest.mark.supported(
    only_if=lambda backend: backend.signature_hash_supported(hashes.SHA1()),
    skip_message="Does not support SHA-1 signature.",
)
class TestDSACertificateRequest:
    @pytest.mark.parametrize(
        ("path", "loader_func"),
        [
            [
                os.path.join("x509", "requests", "dsa_sha1.pem"),
                x509.load_pem_x509_csr,
            ],
            [
                os.path.join("x509", "requests", "dsa_sha1.der"),
                x509.load_der_x509_csr,
            ],
        ],
    )
    def test_load_dsa_request(self, path, loader_func):
        request = _load_cert(path, loader_func)
        assert isinstance(request.signature_hash_algorithm, hashes.SHA1)
        public_key = request.public_key()
        assert isinstance(public_key, dsa.DSAPublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
        ]

    def test_signature(self):
        request = _load_cert(
            os.path.join("x509", "requests", "dsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.signature == binascii.unhexlify(
            b"302c021461d58dc028d0110818a7d817d74235727c4acfdf0214097b52e198e"
            b"ce95de17273f0a924df23ce9d8188"
        )

    def test_tbs_certrequest_bytes(self):
        request = _load_cert(
            os.path.join("x509", "requests", "dsa_sha1.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.tbs_certrequest_bytes == binascii.unhexlify(
            b"3082021802010030573118301606035504030c0f63727970746f677261706879"
            b"2e696f310d300b060355040a0c0450794341310b300906035504061302555331"
            b"0e300c06035504080c055465786173310f300d06035504070c0641757374696e"
            b"308201b63082012b06072a8648ce3804013082011e028181008d7fadbc09e284"
            b"aafa69154cea24177004909e519f8b35d685cde5b4ecdc9583e74d370a0f88ad"
            b"a98f026f27762fb3d5da7836f986dfcdb3589e5b925bea114defc03ef81dae30"
            b"c24bbc6df3d588e93427bba64203d4a5b1687b2b5e3b643d4c614976f89f95a3"
            b"8d3e4c89065fba97514c22c50adbbf289163a74b54859b35b7021500835de56b"
            b"d07cf7f82e2032fe78949aed117aa2ef0281801f717b5a07782fc2e4e68e311f"
            b"ea91a54edd36b86ac634d14f05a68a97eae9d2ef31fb1ef3de42c3d100df9ca6"
            b"4f5bdc2aec7bfdfb474cf831fea05853b5e059f2d24980a0ac463f1e818af352"
            b"3e3cb79a39d45fa92731897752842469cf8540b01491024eaafbce6018e8a1f4"
            b"658c343f4ba7c0b21e5376a21f4beb8491961e038184000281800713f07641f6"
            b"369bb5a9545274a2d4c01998367fb371bb9e13436363672ed68f82174c2de05c"
            b"8e839bc6de568dd50ba28d8d9d8719423aaec5557df10d773ab22d6d65cbb878"
            b"04a697bc8fd965b952f9f7e850edf13c8acdb5d753b6d10e59e0b5732e3c82ba"
            b"fa140342bc4a3bba16bd0681c8a6a2dbbb7efe6ce2b8463b170ba000"
        )
        assert request.signature_hash_algorithm is not None
        public_key = request.public_key()
        assert isinstance(public_key, dsa.DSAPublicKey)
        public_key.verify(
            request.signature,
            request.tbs_certrequest_bytes,
            request.signature_hash_algorithm,
        )


class TestGOSTCertificate:
    def test_numeric_string_x509_name_entry(self):
        cert = _load_cert(
            os.path.join("x509", "e-trust.ru.der"),
            x509.load_der_x509_certificate,
        )
        assert (
            cert.subject.get_attributes_for_oid(
                x509.ObjectIdentifier("1.2.643.3.131.1.1")
            )[0].value
            == "007710474375"
        )


class TestECDSACertificate:
    def test_load_ecdsa_cert(self, backend):
        _skip_curve_unsupported(backend, ec.SECP384R1())
        cert = _load_cert(
            os.path.join("x509", "ecdsa_root.pem"),
            x509.load_pem_x509_certificate,
        )
        assert isinstance(cert.signature_hash_algorithm, hashes.SHA384)
        public_key = cert.public_key()
        assert isinstance(public_key, ec.EllipticCurvePublicKey)
        num = public_key.public_numbers()
        assert num.x == int(
            "dda7d9bb8ab80bfb0b7f21d2f0bebe73f3335d1abc34eadec69bbcd095f"
            "6f0ccd00bba615b51467e9e2d9fee8e630c17",
            16,
        )
        assert num.y == int(
            "ec0770f5cf842e40839ce83f416d3badd3a4145936789d0343ee10136c7"
            "2deae88a7a16bb543ce67dc23ff031ca3e23e",
            16,
        )
        assert isinstance(num.curve, ec.SECP384R1)
        assert isinstance(cert.signature_algorithm_parameters, ec.ECDSA)
        assert isinstance(
            cert.signature_algorithm_parameters.algorithm, hashes.SHA384
        )
        public_key.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            cert.signature_algorithm_parameters,
        )

    def test_load_ecdsa_cert_null_alg_params(self):
        """
        This test verifies that we reject certificates with encoded null
        parameters in the ECDSA signature AlgorithmIdentifier. This is invalid;
        Java 11 (up to at least 11.0.19) generated certificates with this
        encoding, but we no longer tolerate it.
        """
        with pytest.raises(ValueError):
            _load_cert(
                os.path.join("x509", "custom", "ecdsa_null_alg.pem"),
                x509.load_pem_x509_certificate,
            )

    def test_load_bitstring_dn(self):
        cert = _load_cert(
            os.path.join("x509", "scottishpower-bitstring-dn.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.subject == x509.Name(
            [
                x509.NameAttribute(x509.NameOID.COMMON_NAME, "ScottishPower"),
                x509.NameAttribute(
                    x509.NameOID.ORGANIZATIONAL_UNIT_NAME, "02"
                ),
                x509.NameAttribute(
                    NameOID.X500_UNIQUE_IDENTIFIER,
                    b"\x00\x70\xb3\xd5\x1f\x30\x5f\x00\x01",
                    _ASN1Type.BitString,
                ),
            ]
        )
        assert repr(cert.subject) == (
            "<Name(2.5.4.45=#0070b3d51f305f0001,OU=02,CN=ScottishPower)>"
        )

    def test_load_name_attribute_long_form_asn1_tag(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "long-form-name-attribute.pem"),
            x509.load_pem_x509_certificate,
        )
        with pytest.raises(ValueError, match="Long-form"):
            cert.subject
        with pytest.raises(ValueError, match="Long-form"):
            cert.issuer

    def test_ms_certificate_template(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "ms-certificate-template.pem"),
            x509.load_pem_x509_certificate,
        )
        ext = cert.extensions.get_extension_for_class(
            x509.MSCertificateTemplate
        )
        tpl = ext.value
        assert isinstance(tpl, x509.MSCertificateTemplate)
        assert tpl == x509.MSCertificateTemplate(
            template_id=x509.ObjectIdentifier("1.2.3.4.5.6.7.8.9.0"),
            major_version=1,
            minor_version=None,
        )

    def test_signature(self):
        cert = _load_cert(
            os.path.join("x509", "ecdsa_root.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.signature == binascii.unhexlify(
            b"3065023100adbcf26c3f124ad12d39c30a099773f488368c8827bbe6888d5085"
            b"a763f99e32de66930ff1ccb1098fdd6cabfa6b7fa0023039665bc2648db89e50"
            b"dca8d549a2edc7dcd1497f1701b8c8868f4e8c882ba89aa98ac5d100bdf854e2"
            b"9ae55b7cb32717"
        )
        r, s = decode_dss_signature(cert.signature)
        assert r == int(
            "adbcf26c3f124ad12d39c30a099773f488368c8827bbe6888d5085a763f99e32"
            "de66930ff1ccb1098fdd6cabfa6b7fa0",
            16,
        )
        assert s == int(
            "39665bc2648db89e50dca8d549a2edc7dcd1497f1701b8c8868f4e8c882ba89a"
            "a98ac5d100bdf854e29ae55b7cb32717",
            16,
        )

    def test_tbs_certificate_bytes(self, backend):
        _skip_curve_unsupported(backend, ec.SECP384R1())
        cert = _load_cert(
            os.path.join("x509", "ecdsa_root.pem"),
            x509.load_pem_x509_certificate,
        )
        assert cert.tbs_certificate_bytes == binascii.unhexlify(
            b"308201c5a0030201020210055556bcf25ea43535c3a40fd5ab4572300a06082"
            b"a8648ce3d0403033061310b300906035504061302555331153013060355040a"
            b"130c446967694365727420496e6331193017060355040b13107777772e64696"
            b"769636572742e636f6d3120301e06035504031317446967694365727420476c"
            b"6f62616c20526f6f74204733301e170d3133303830313132303030305a170d3"
            b"338303131353132303030305a3061310b300906035504061302555331153013"
            b"060355040a130c446967694365727420496e6331193017060355040b1310777"
            b"7772e64696769636572742e636f6d3120301e06035504031317446967694365"
            b"727420476c6f62616c20526f6f742047333076301006072a8648ce3d0201060"
            b"52b8104002203620004dda7d9bb8ab80bfb0b7f21d2f0bebe73f3335d1abc34"
            b"eadec69bbcd095f6f0ccd00bba615b51467e9e2d9fee8e630c17ec0770f5cf8"
            b"42e40839ce83f416d3badd3a4145936789d0343ee10136c72deae88a7a16bb5"
            b"43ce67dc23ff031ca3e23ea3423040300f0603551d130101ff040530030101f"
            b"f300e0603551d0f0101ff040403020186301d0603551d0e04160414b3db48a4"
            b"f9a1c5d8ae3641cc1163696229bc4bc6"
        )
        assert cert.signature_hash_algorithm is not None
        public_key = cert.public_key()
        assert isinstance(public_key, ec.EllipticCurvePublicKey)
        public_key.verify(
            cert.signature,
            cert.tbs_certificate_bytes,
            ec.ECDSA(cert.signature_hash_algorithm),
        )

    def test_load_ecdsa_no_named_curve(self, backend):
        _skip_curve_unsupported(backend, ec.SECP256R1())
        cert = _load_cert(
            os.path.join("x509", "custom", "ec_no_named_curve.pem"),
            x509.load_pem_x509_certificate,
        )
        # We map explicit parameters to known curves and this cert
        # contains explicit params for P256, so it should load.
        pk = cert.public_key()
        assert isinstance(pk, ec.EllipticCurvePublicKey)
        assert isinstance(pk.curve, ec.SECP256R1)

    def test_verify_directly_issued_by_ec(self):
        issuer_private_key = ec.generate_private_key(ec.SECP256R1())
        subject_private_key = ec.generate_private_key(ec.SECP256R1())
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_ec_bad_sig(self):
        issuer_private_key = ec.generate_private_key(ec.SECP256R1())
        subject_private_key = ec.generate_private_key(ec.SECP256R1())
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert_bad_sig = _break_cert_sig(cert)
        with pytest.raises(InvalidSignature):
            cert_bad_sig.verify_directly_issued_by(ca)


class TestECDSACertificateRequest:
    @pytest.mark.parametrize(
        ("path", "loader_func"),
        [
            [
                os.path.join("x509", "requests", "ec_sha256.pem"),
                x509.load_pem_x509_csr,
            ],
            [
                os.path.join("x509", "requests", "ec_sha256.der"),
                x509.load_der_x509_csr,
            ],
        ],
    )
    def test_load_ecdsa_certificate_request(self, path, loader_func, backend):
        _skip_curve_unsupported(backend, ec.SECP384R1())
        request = _load_cert(path, loader_func)
        assert isinstance(request.signature_hash_algorithm, hashes.SHA256)
        public_key = request.public_key()
        assert isinstance(public_key, ec.EllipticCurvePublicKey)
        subject = request.subject
        assert isinstance(subject, x509.Name)
        assert list(subject) == [
            x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
            x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "Texas"),
            x509.NameAttribute(NameOID.LOCALITY_NAME, "Austin"),
        ]

    def test_signature(self, backend):
        _skip_curve_unsupported(backend, ec.SECP384R1())
        request = _load_cert(
            os.path.join("x509", "requests", "ec_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.signature == binascii.unhexlify(
            b"306502302c1a9f7de8c1787332d2307a886b476a59f172b9b0e250262f3238b1"
            b"b45ee112bb6eb35b0fb56a123b9296eb212dffc302310094cf440c95c52827d5"
            b"56ae6d76500e3008255d47c29f7ee782ed7558e51bfd76aa45df6d999ed5c463"
            b"347fe2382d1751"
        )

    def test_tbs_certrequest_bytes(self, backend):
        _skip_curve_unsupported(backend, ec.SECP384R1())
        request = _load_cert(
            os.path.join("x509", "requests", "ec_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        assert request.tbs_certrequest_bytes == binascii.unhexlify(
            b"3081d602010030573118301606035504030c0f63727970746f6772617068792"
            b"e696f310d300b060355040a0c0450794341310b300906035504061302555331"
            b"0e300c06035504080c055465786173310f300d06035504070c0641757374696"
            b"e3076301006072a8648ce3d020106052b8104002203620004de19b514c0b3c3"
            b"ae9b398ea3e26b5e816bdcf9102cad8f12fe02f9e4c9248724b39297ed7582e"
            b"04d8b32a551038d09086803a6d3fb91a1a1167ec02158b00efad39c9396462f"
            b"accff0ffaf7155812909d3726bd59fde001cff4bb9b2f5af8cbaa000"
        )
        assert request.signature_hash_algorithm is not None
        public_key = request.public_key()
        assert isinstance(public_key, ec.EllipticCurvePublicKey)
        public_key.verify(
            request.signature,
            request.tbs_certrequest_bytes,
            ec.ECDSA(request.signature_hash_algorithm),
        )


class TestOtherCertificate:
    def test_unsupported_subject_public_key_info(self):
        cert = _load_cert(
            os.path.join(
                "x509", "custom", "unsupported_subject_public_key_info.pem"
            ),
            x509.load_pem_x509_certificate,
        )

        with pytest.raises(UnsupportedAlgorithm):
            cert.public_key()

    def test_bad_time_in_validity(self):
        with pytest.raises(ValueError, match="Validity::not_after"):
            _load_cert(
                os.path.join("x509", "badasn1time.pem"),
                x509.load_pem_x509_certificate,
            )

    def test_invalid_empty_eku(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "empty-eku.pem"),
            x509.load_pem_x509_certificate,
        )

        with pytest.raises(ValueError, match="InvalidSize"):
            cert.extensions.get_extension_for_class(ExtendedKeyUsage)

    def test_invalid_empty_subject_alternative_name(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "empty-san.pem"),
            x509.load_pem_x509_certificate,
        )

        with pytest.raises(ValueError, match="at least one GeneralName"):
            cert.extensions.get_extension_for_class(
                x509.SubjectAlternativeName
            )

    def test_invalid_empty_issuer_alternative_name(self):
        cert = _load_cert(
            os.path.join("x509", "custom", "empty-ian.pem"),
            x509.load_pem_x509_certificate,
        )

        with pytest.raises(ValueError, match="at least one GeneralName"):
            cert.extensions.get_extension_for_class(x509.IssuerAlternativeName)


class TestNameAttribute:
    EXPECTED_TYPES: typing.ClassVar[
        list[tuple[x509.ObjectIdentifier, _ASN1Type]]
    ] = [
        (NameOID.COMMON_NAME, _ASN1Type.UTF8String),
        (NameOID.COUNTRY_NAME, _ASN1Type.PrintableString),
        (NameOID.LOCALITY_NAME, _ASN1Type.UTF8String),
        (NameOID.STATE_OR_PROVINCE_NAME, _ASN1Type.UTF8String),
        (NameOID.STREET_ADDRESS, _ASN1Type.UTF8String),
        (NameOID.ORGANIZATION_NAME, _ASN1Type.UTF8String),
        (NameOID.ORGANIZATIONAL_UNIT_NAME, _ASN1Type.UTF8String),
        (NameOID.SERIAL_NUMBER, _ASN1Type.PrintableString),
        (NameOID.SURNAME, _ASN1Type.UTF8String),
        (NameOID.GIVEN_NAME, _ASN1Type.UTF8String),
        (NameOID.TITLE, _ASN1Type.UTF8String),
        (NameOID.GENERATION_QUALIFIER, _ASN1Type.UTF8String),
        (NameOID.X500_UNIQUE_IDENTIFIER, _ASN1Type.UTF8String),
        (NameOID.DN_QUALIFIER, _ASN1Type.PrintableString),
        (NameOID.PSEUDONYM, _ASN1Type.UTF8String),
        (NameOID.USER_ID, _ASN1Type.UTF8String),
        (NameOID.DOMAIN_COMPONENT, _ASN1Type.IA5String),
        (NameOID.EMAIL_ADDRESS, _ASN1Type.IA5String),
        (NameOID.JURISDICTION_COUNTRY_NAME, _ASN1Type.PrintableString),
        (NameOID.JURISDICTION_LOCALITY_NAME, _ASN1Type.UTF8String),
        (NameOID.JURISDICTION_STATE_OR_PROVINCE_NAME, _ASN1Type.UTF8String),
        (NameOID.BUSINESS_CATEGORY, _ASN1Type.UTF8String),
        (NameOID.POSTAL_ADDRESS, _ASN1Type.UTF8String),
        (NameOID.POSTAL_CODE, _ASN1Type.UTF8String),
    ]

    def test_default_types(self):
        for oid, asn1_type in TestNameAttribute.EXPECTED_TYPES:
            na = x509.NameAttribute(oid, "US")
            assert na._type == asn1_type

    def test_alternate_type(self):
        na2 = x509.NameAttribute(
            NameOID.COMMON_NAME, "common", _ASN1Type.IA5String
        )
        assert na2._type == _ASN1Type.IA5String

    def test_init_bad_oid(self):
        with pytest.raises(TypeError):
            x509.NameAttribute(
                typing.cast(typing.Any, None),
                "value",
            )

    def test_init_bad_value(self):
        with pytest.raises(TypeError):
            x509.NameAttribute(
                x509.ObjectIdentifier("2.999.1"),
                b"bytes",
            )

    def test_init_bitstring_not_bytes(self):
        with pytest.raises(TypeError):
            x509.NameAttribute(
                x509.ObjectIdentifier("2.5.4.45"), "str", _ASN1Type.BitString
            )

    def test_init_bitstring_not_allowed_random_oid(self):
        # We only allow BitString type with X500_UNIQUE_IDENTIFIER
        with pytest.raises(TypeError):
            x509.NameAttribute(
                x509.NameOID.COMMON_NAME, b"ok", _ASN1Type.BitString
            )

    def test_init_none_value(self):
        with pytest.raises(TypeError):
            x509.NameAttribute(
                NameOID.ORGANIZATION_NAME,
                typing.cast(typing.Any, None),
            )

    def test_init_bad_length(self):
        with pytest.raises(ValueError):
            x509.NameAttribute(NameOID.COUNTRY_NAME, "United States")

        # unicode string of length 2, but > 2 bytes
        with pytest.raises(ValueError):
            x509.NameAttribute(NameOID.COUNTRY_NAME, "\U0001f37a\U0001f37a")

        with pytest.raises(ValueError):
            x509.NameAttribute(NameOID.JURISDICTION_COUNTRY_NAME, "Too Long")
        with pytest.raises(ValueError):
            x509.NameAttribute(NameOID.COMMON_NAME, "Too Long" * 10)
        with pytest.raises(ValueError):
            x509.NameAttribute(NameOID.COMMON_NAME, "")

    def test_invalid_type(self):
        with pytest.raises(TypeError):
            x509.NameAttribute(
                NameOID.COMMON_NAME,
                "common",
                typing.cast(typing.Any, "notanenum"),
            )

    def test_eq(self):
        assert x509.NameAttribute(
            x509.ObjectIdentifier("2.999.1"), "value"
        ) == x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value")

    def test_ne(self):
        assert x509.NameAttribute(
            x509.ObjectIdentifier("2.5.4.3"), "value"
        ) != x509.NameAttribute(x509.ObjectIdentifier("2.5.4.5"), "value")
        assert x509.NameAttribute(
            x509.ObjectIdentifier("2.999.1"), "value"
        ) != x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value2")
        assert (
            x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value")
            != object()
        )

    def test_repr(self):
        na = x509.NameAttribute(x509.ObjectIdentifier("2.5.4.3"), "value")
        assert repr(na) == (
            "<NameAttribute(oid=<ObjectIdentifier(oid=2.5.4.3, name=commo"
            "nName)>, value='value')>"
        )

    def test_distinguished_name(self):
        # Escaping
        na = x509.NameAttribute(NameOID.COMMON_NAME, 'James "Jim" Smith, III')
        assert na.rfc4514_string() == r"CN=James \"Jim\" Smith\, III"
        na = x509.NameAttribute(NameOID.USER_ID, "# escape+,;\0this ")
        assert na.rfc4514_string() == r"UID=\# escape\+\,\;\00this\ "

        # Nonstandard attribute OID
        na = x509.NameAttribute(NameOID.BUSINESS_CATEGORY, "banking")
        assert na.rfc4514_string() == "2.5.4.15=banking"

        # non-utf8 attribute (bitstring with raw bytes)
        na_bytes = x509.NameAttribute(
            x509.ObjectIdentifier("2.5.4.45"),
            b"\x01\x02\x03\x04",
            _ASN1Type.BitString,
        )
        assert na_bytes.rfc4514_string() == "2.5.4.45=#01020304"

    def test_distinguished_name_custom_attrs(self):
        name = x509.Name(
            [
                x509.NameAttribute(NameOID.EMAIL_ADDRESS, "santa@north.pole"),
                x509.NameAttribute(NameOID.COMMON_NAME, "Santa Claus"),
            ]
        )
        assert name.rfc4514_string({}) == (
            "CN=Santa Claus,1.2.840.113549.1.9.1=santa@north.pole"
        )
        assert name.rfc4514_string({NameOID.EMAIL_ADDRESS: "E"}) == (
            "CN=Santa Claus,E=santa@north.pole"
        )
        assert name.rfc4514_string(
            {NameOID.COMMON_NAME: "CommonName", NameOID.EMAIL_ADDRESS: "E"}
        ) == ("CommonName=Santa Claus,E=santa@north.pole")

    def test_empty_name(self):
        assert x509.Name([]).rfc4514_string() == ""

    def test_empty_value(self):
        na = x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, "")
        assert na.rfc4514_string() == r"ST="


class TestRelativeDistinguishedName:
    def test_init_empty(self):
        with pytest.raises(ValueError):
            x509.RelativeDistinguishedName([])

    def test_init_not_nameattribute(self):
        with pytest.raises(TypeError):
            x509.RelativeDistinguishedName(
                [typing.cast(typing.Any, "not-a-NameAttribute")]
            )

    def test_init_duplicate_attribute(self):
        with pytest.raises(ValueError):
            x509.RelativeDistinguishedName(
                [
                    x509.NameAttribute(
                        x509.ObjectIdentifier("2.999.1"), "val1"
                    ),
                    x509.NameAttribute(
                        x509.ObjectIdentifier("2.999.1"), "val1"
                    ),
                ]
            )

    def test_hash(self):
        rdn1 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2"),
            ]
        )
        rdn2 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
            ]
        )
        rdn3 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value3"),
            ]
        )
        assert hash(rdn1) == hash(rdn2)
        assert hash(rdn1) != hash(rdn3)

    def test_eq(self):
        rdn1 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2"),
            ]
        )
        rdn2 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
            ]
        )
        assert rdn1 == rdn2

    def test_ne(self):
        rdn1 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2"),
            ]
        )
        rdn2 = x509.RelativeDistinguishedName(
            [
                x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
                x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value3"),
            ]
        )
        assert rdn1 != rdn2
        assert rdn1 != object()

    def test_iter_input(self):
        # Order must be preserved too
        attrs = [
            x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1"),
            x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value2"),
            x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value3"),
        ]
        rdn = x509.RelativeDistinguishedName(iter(attrs))
        assert list(rdn) == attrs
        assert list(rdn) == attrs

    def test_get_attributes_for_oid(self):
        oid = x509.ObjectIdentifier("2.999.1")
        attr = x509.NameAttribute(oid, "value1")
        rdn = x509.RelativeDistinguishedName([attr])
        assert rdn.get_attributes_for_oid(oid) == [attr]
        assert rdn.get_attributes_for_oid(x509.ObjectIdentifier("1.2.3")) == []


class TestObjectIdentifier:
    def test_eq(self):
        oid1 = x509.ObjectIdentifier("2.999.1")
        oid2 = x509.ObjectIdentifier("2.999.1")
        assert oid1 == oid2

    def test_ne(self):
        oid1 = x509.ObjectIdentifier("2.999.1")
        assert oid1 != x509.ObjectIdentifier("2.999.2")
        assert oid1 != object()

    def test_comparison(self):
        oid1 = x509.ObjectIdentifier("2.999.1")
        oid2 = x509.ObjectIdentifier("2.999.2")
        with pytest.raises(TypeError):
            oid1 < oid2  # type: ignore[operator]

    def test_repr(self):
        oid = x509.ObjectIdentifier("2.5.4.3")
        assert repr(oid) == "<ObjectIdentifier(oid=2.5.4.3, name=commonName)>"
        oid = x509.ObjectIdentifier("2.999.1")
        assert repr(oid) == "<ObjectIdentifier(oid=2.999.1, name=Unknown OID)>"

    def test_name_property(self):
        oid = x509.ObjectIdentifier("2.5.4.3")
        assert oid._name == "commonName"
        oid = x509.ObjectIdentifier("2.999.1")
        assert oid._name == "Unknown OID"

    def test_too_short(self):
        with pytest.raises(ValueError):
            x509.ObjectIdentifier("1")

    def test_invalid_input(self):
        with pytest.raises(ValueError):
            x509.ObjectIdentifier("notavalidform")

    def test_invalid_node1(self):
        with pytest.raises(ValueError):
            x509.ObjectIdentifier("7.1.37")

    def test_invalid_node2(self):
        with pytest.raises(ValueError):
            x509.ObjectIdentifier("1.50.200")

    def test_valid(self):
        x509.ObjectIdentifier("0.35.200")
        x509.ObjectIdentifier("1.39.999")
        x509.ObjectIdentifier("2.5.29.3")
        x509.ObjectIdentifier("2.999.37.5.22.8")
        x509.ObjectIdentifier(f"2.25.{2**128 - 1}")

    def test_oid_arc_too_large(self):
        with pytest.raises(ValueError):
            x509.ObjectIdentifier(f"2.25.{2**128}")


class TestName:
    def test_eq(self):
        ava1 = x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1")
        ava2 = x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2")
        name1 = x509.Name([ava1, ava2])
        name2 = x509.Name(
            [
                x509.RelativeDistinguishedName([ava1]),
                x509.RelativeDistinguishedName([ava2]),
            ]
        )
        name3 = x509.Name([x509.RelativeDistinguishedName([ava1, ava2])])
        name4 = x509.Name([x509.RelativeDistinguishedName([ava2, ava1])])
        assert name1 == name2
        assert name3 == name4

    def test_ne(self):
        ava1 = x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1")
        ava2 = x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2")
        name1 = x509.Name([ava1, ava2])
        name2 = x509.Name([ava2, ava1])
        name3 = x509.Name([x509.RelativeDistinguishedName([ava1, ava2])])
        assert name1 != name2
        assert name1 != name3
        assert name1 != object()

    def test_hash(self):
        ava1 = x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1")
        ava2 = x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2")
        name1 = x509.Name([ava1, ava2])
        name2 = x509.Name(
            [
                x509.RelativeDistinguishedName([ava1]),
                x509.RelativeDistinguishedName([ava2]),
            ]
        )
        name3 = x509.Name([ava2, ava1])
        name4 = x509.Name([x509.RelativeDistinguishedName([ava1, ava2])])
        name5 = x509.Name([x509.RelativeDistinguishedName([ava2, ava1])])
        assert hash(name1) == hash(name2)
        assert hash(name1) != hash(name3)
        assert hash(name1) != hash(name4)
        assert hash(name4) == hash(name5)

    def test_iter_input(self):
        attrs = [
            x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1")
        ]
        name = x509.Name(iter(attrs))
        assert list(name) == attrs
        assert list(name) == attrs

    def test_rdns(self):
        rdn1 = x509.NameAttribute(x509.ObjectIdentifier("2.999.1"), "value1")
        rdn2 = x509.NameAttribute(x509.ObjectIdentifier("2.999.2"), "value2")
        name1 = x509.Name([rdn1, rdn2])
        assert name1.rdns == [
            x509.RelativeDistinguishedName([rdn1]),
            x509.RelativeDistinguishedName([rdn2]),
        ]
        name2 = x509.Name([x509.RelativeDistinguishedName([rdn1, rdn2])])
        assert name2.rdns == [x509.RelativeDistinguishedName([rdn1, rdn2])]

    @pytest.mark.parametrize(
        ("common_name", "org_name", "expected_repr"),
        [
            (
                "cryptography.io",
                "PyCA",
                "<Name(O=PyCA,CN=cryptography.io)>",
            ),
            (
                "Certificación",
                "Certificación",
                "<Name(O=Certificación,CN=Certificación)>",
            ),
        ],
    )
    def test_repr(self, common_name, org_name, expected_repr):
        name = x509.Name(
            [
                x509.NameAttribute(NameOID.COMMON_NAME, common_name),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, org_name),
            ]
        )

        assert repr(name) == expected_repr

    def test_rfc4514_attribute_name(self):
        a = x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io")
        assert a.rfc4514_attribute_name == "CN"
        b = x509.NameAttribute(NameOID.PSEUDONYM, "cryptography.io")
        assert b.rfc4514_attribute_name == "2.5.4.65"

    def test_rfc4514_string(self):
        n = x509.Name(
            [
                x509.RelativeDistinguishedName(
                    [x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "net")]
                ),
                x509.RelativeDistinguishedName(
                    [x509.NameAttribute(NameOID.DOMAIN_COMPONENT, "example")]
                ),
                x509.RelativeDistinguishedName(
                    [
                        x509.NameAttribute(
                            NameOID.ORGANIZATIONAL_UNIT_NAME, "Sales"
                        ),
                        x509.NameAttribute(NameOID.COMMON_NAME, "J.  Smith"),
                    ]
                ),
            ]
        )
        assert n.rfc4514_string() == "OU=Sales+CN=J.  Smith,DC=example,DC=net"

    def test_rfc4514_string_empty_values(self):
        n = x509.Name(
            [
                x509.NameAttribute(NameOID.COUNTRY_NAME, "US"),
                x509.NameAttribute(NameOID.STATE_OR_PROVINCE_NAME, ""),
                x509.NameAttribute(NameOID.LOCALITY_NAME, ""),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
                x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
            ]
        )
        assert n.rfc4514_string() == "CN=cryptography.io,O=PyCA,L=,ST=,C=US"

    def test_not_nameattribute(self):
        with pytest.raises(TypeError):
            x509.Name([typing.cast(typing.Any, "not-a-NameAttribute")])

    def test_bytes(self):
        name = x509.Name(
            [
                x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            ]
        )
        assert name.public_bytes() == binascii.unhexlify(
            b"30293118301606035504030c0f63727970746f6772617068792e696f310d300"
            b"b060355040a0c0450794341"
        )

    def test_from_bytes(self):
        data = binascii.unhexlify(
            b"30293118301606035504030c0f63727970746f6772617068792e696f310d"
            b"300b060355040a0c0450794341"
        )
        name = x509.Name.from_bytes(data)
        assert name == x509.Name(
            [
                x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            ]
        )
        assert name.public_bytes() == data

    @pytest.mark.parametrize(
        "data",
        [
            # Empty.
            b"",
            # Not valid DER.
            b"\x00\x01\x02",
            # Wrong tag (SET instead of SEQUENCE).
            b"\x31\x00",
            # Trailing data after the name.
            binascii.unhexlify(b"300000"),
            # RDN with a UTF8String value that is not valid UTF-8.
            binascii.unhexlify(b"300c310a300806035504030c01ff"),
        ],
    )
    def test_from_bytes_invalid(self, data):
        with pytest.raises(ValueError):
            x509.Name.from_bytes(data)

    def test_bitstring_encoding(self):
        name = x509.Name(
            [
                x509.NameAttribute(NameOID.COMMON_NAME, "cryptography.io"),
                x509.NameAttribute(
                    x509.ObjectIdentifier("2.5.4.45"),
                    b"\x01\x02",
                    _ASN1Type.BitString,
                ),
            ]
        )
        assert name.public_bytes() == binascii.unhexlify(
            b"30273118301606035504030c0f63727970746f6772617068792e696f310b3"
            b"009060355042d03020102"
        )

    def test_bmpstring_bytes(self):
        # For this test we need an odd length string. BMPString is UCS-2
        # encoded so it will always be even length and OpenSSL will error if
        # you pass an odd length string without encoding it properly first.
        name = x509.Name(
            [
                x509.NameAttribute(
                    NameOID.COMMON_NAME,
                    "cryptography.io",
                    _ASN1Type.BMPString,
                ),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            ]
        )
        assert name.public_bytes() == binascii.unhexlify(
            b"30383127302506035504031e1e00630072007900700074006f00670072006100"
            b"7000680079002e0069006f310d300b060355040a0c0450794341"
        )

    def test_universalstring_bytes(self):
        # UniversalString is UCS-4
        name = x509.Name(
            [
                x509.NameAttribute(
                    NameOID.COMMON_NAME,
                    "cryptography.io",
                    _ASN1Type.UniversalString,
                ),
                x509.NameAttribute(NameOID.ORGANIZATION_NAME, "PyCA"),
            ]
        )
        assert name.public_bytes() == binascii.unhexlify(
            b"30563145304306035504031c3c00000063000000720000007900000070000000"
            b"740000006f000000670000007200000061000000700000006800000079000000"
            b"2e000000690000006f310d300b060355040a0c0450794341"
        )


class TestEd25519Certificate:
    def test_load_pem_cert(self):
        cert = _load_cert(
            os.path.join("x509", "ed25519", "root-ed25519.pem"),
            x509.load_pem_x509_certificate,
        )
        # self-signed, so this will work
        public_key = cert.public_key()
        assert isinstance(public_key, ed25519.Ed25519PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ED25519
        public_key.verify(cert.signature, cert.tbs_certificate_bytes)
        assert isinstance(cert, x509.Certificate)
        assert cert.serial_number == 9579446940964433301
        assert cert.signature_hash_algorithm is None
        assert cert.signature_algorithm_oid == SignatureAlgorithmOID.ED25519
        assert cert.signature_algorithm_parameters is None

    def test_deepcopy(self):
        cert = _load_cert(
            os.path.join("x509", "ed25519", "root-ed25519.pem"),
            x509.load_pem_x509_certificate,
        )
        assert copy.deepcopy(cert) is cert

    def test_verify_directly_issued_by_ed25519(self):
        issuer_private_key = ed25519.Ed25519PrivateKey.generate()
        subject_private_key = ed25519.Ed25519PrivateKey.generate()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_ed25519_bad_sig(self):
        issuer_private_key = ed25519.Ed25519PrivateKey.generate()
        subject_private_key = ed25519.Ed25519PrivateKey.generate()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert_bad_sig = _break_cert_sig(cert)
        with pytest.raises(InvalidSignature):
            cert_bad_sig.verify_directly_issued_by(ca)


@pytest.mark.supported(
    only_if=lambda backend: backend.ed448_supported(),
    skip_message="Requires OpenSSL with Ed448 support",
)
class TestEd448Certificate:
    def test_load_pem_cert(self):
        cert = _load_cert(
            os.path.join("x509", "ed448", "root-ed448.pem"),
            x509.load_pem_x509_certificate,
        )
        # self-signed, so this will work
        public_key = cert.public_key()
        assert isinstance(public_key, ed448.Ed448PublicKey)
        assert cert.public_key_algorithm_oid == PublicKeyAlgorithmOID.ED448
        public_key.verify(cert.signature, cert.tbs_certificate_bytes)
        assert isinstance(cert, x509.Certificate)
        assert cert.serial_number == 448
        assert cert.signature_hash_algorithm is None
        assert cert.signature_algorithm_oid == SignatureAlgorithmOID.ED448
        assert cert.signature_algorithm_parameters is None

    def test_verify_directly_issued_by_ed448(self):
        issuer_private_key = ed448.Ed448PrivateKey.generate()
        subject_private_key = ed448.Ed448PrivateKey.generate()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_ed448_bad_sig(self):
        issuer_private_key = ed448.Ed448PrivateKey.generate()
        subject_private_key = ed448.Ed448PrivateKey.generate()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert_bad_sig = _break_cert_sig(cert)
        with pytest.raises(InvalidSignature):
            cert_bad_sig.verify_directly_issued_by(ca)


@pytest.mark.supported(
    only_if=lambda backend: backend.mldsa_supported(),
    skip_message="Requires a backend with ML-DSA support",
)
@pytest.mark.parametrize(
    ("priv_key_cls", "pub_key_cls", "sig_oid"),
    [
        (
            mldsa.MLDSA44PrivateKey,
            mldsa.MLDSA44PublicKey,
            SignatureAlgorithmOID.ML_DSA_44,
        ),
        (
            mldsa.MLDSA65PrivateKey,
            mldsa.MLDSA65PublicKey,
            SignatureAlgorithmOID.ML_DSA_65,
        ),
        (
            mldsa.MLDSA87PrivateKey,
            mldsa.MLDSA87PublicKey,
            SignatureAlgorithmOID.ML_DSA_87,
        ),
    ],
)
class TestMLDSACertificate:
    def test_sign_and_verify_directly_issued_by_mldsa(
        self, priv_key_cls, pub_key_cls, sig_oid
    ):
        issuer_private_key = priv_key_cls.generate()
        subject_private_key = priv_key_cls.generate()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        assert cert.signature_algorithm_oid == sig_oid
        assert cert.signature_hash_algorithm is None
        assert isinstance(cert.public_key(), pub_key_cls)
        cert.verify_directly_issued_by(ca)

    def test_verify_directly_issued_by_mldsa_bad_sig(
        self, priv_key_cls, pub_key_cls, sig_oid
    ):
        issuer_private_key = priv_key_cls.generate()
        subject_private_key = priv_key_cls.generate()
        ca, cert = _generate_ca_and_leaf(
            issuer_private_key, subject_private_key
        )
        cert_bad_sig = _break_cert_sig(cert)
        with pytest.raises(InvalidSignature):
            cert_bad_sig.verify_directly_issued_by(ca)


@pytest.mark.supported(
    only_if=lambda backend: backend.dh_supported(),
    skip_message="DH not supported",
)
class TestSignatureRejection:
    """Test if signing rejects DH keys properly."""

    def load_key(self):
        vector = load_vectors_from_file(
            os.path.join("asymmetric", "DH", "rfc3526.txt"),
            load_nist_vectors,
        )[1]
        p = int.from_bytes(binascii.unhexlify(vector["p"]), "big")
        with pytest.warns(utils.DeprecatedIn50):
            params = dh.DHParameterNumbers(p, int(vector["g"]))
        param = params.parameters()
        return param.generate_private_key()

    def test_crt_signing_check(self, rsa_key_2048: rsa.RSAPrivateKey):
        issuer_private_key = self.load_key()
        public_key = rsa_key_2048.public_key()
        not_valid_before = datetime.datetime(2020, 1, 1, 1, 1)
        not_valid_after = datetime.datetime(2050, 12, 31, 8, 30)
        builder = (
            x509.CertificateBuilder()
            .serial_number(777)
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .subject_name(
                x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
            )
            .public_key(public_key)
            .not_valid_before(not_valid_before)
            .not_valid_after(not_valid_after)
        )

        with pytest.raises(TypeError):
            builder.sign(issuer_private_key, hashes.SHA256())

    def test_csr_signing_check(self):
        private_key = self.load_key()
        builder = x509.CertificateSigningRequestBuilder().subject_name(
            x509.Name([x509.NameAttribute(NameOID.COUNTRY_NAME, "US")])
        )

        with pytest.raises(TypeError):
            builder.sign(private_key, hashes.SHA256())

    def test_crl_signing_check(self):
        private_key = self.load_key()
        last_time = (
            datetime.datetime.now().replace(tzinfo=None).replace(microsecond=0)
        )
        next_time = last_time
        builder = (
            x509.CertificateRevocationListBuilder()
            .issuer_name(
                x509.Name([x509.NameAttribute(NameOID.COMMON_NAME, "CA")])
            )
            .last_update(last_time)
            .next_update(next_time)
        )

        with pytest.raises(TypeError):
            builder.sign(private_key, hashes.SHA256())


def test_random_serial_number(monkeypatch):
    sample_data = os.urandom(20)

    def notrandom(size):
        assert size == len(sample_data)
        return sample_data

    monkeypatch.setattr(os, "urandom", notrandom)

    serial_number = x509.random_serial_number()

    assert serial_number == int.from_bytes(sample_data, "big") >> 1
    assert serial_number.bit_length() < 160


class TestAttribute:
    def test_eq(self):
        attr1 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
        )
        attr2 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
        )
        assert attr1 == attr2

    def test_ne(self):
        attr1 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
        )
        attr2 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
            _ASN1Type.IA5String.value,
        )
        attr3 = x509.Attribute(
            x509.oid.AttributeOID.UNSTRUCTURED_NAME,
            b"value",
        )
        attr4 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"other value",
        )
        assert attr1 != attr2
        assert attr1 != attr3
        assert attr1 != attr4
        assert attr1 != object()

    def test_repr(self):
        attr1 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
        )
        assert repr(attr1) == (
            "<Attribute(oid=<ObjectIdentifier(oid=1.2.840.113549.1.9.7, name="
            "challengePassword)>, value=b'value')>"
        )

    def test_hash(self):
        attr1 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
            _ASN1Type.UTF8String.value,
        )
        attr2 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
            _ASN1Type.UTF8String.value,
        )
        attr3 = x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"value",
            _ASN1Type.IA5String.value,
        )
        assert hash(attr1) == hash(attr2)
        assert hash(attr1) != hash(attr3)


class TestAttributes:
    def test_no_attributes(self):
        attrs = x509.Attributes([])
        assert len(attrs) == 0

    def test_get_attribute_for_oid(self):
        attr_list = [
            x509.Attribute(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD,
                b"nonsense",
            ),
            x509.Attribute(
                x509.oid.AttributeOID.UNSTRUCTURED_NAME,
                b"montessori",
                _ASN1Type.PrintableString.value,
            ),
        ]
        attrs = x509.Attributes(attr_list)
        attr = attrs.get_attribute_for_oid(
            x509.oid.AttributeOID.UNSTRUCTURED_NAME
        )
        assert attr.oid == x509.oid.AttributeOID.UNSTRUCTURED_NAME
        assert attr.value == b"montessori"
        assert attr._type == _ASN1Type.PrintableString.value

    def test_indexing(self):
        attr_list = [
            x509.Attribute(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD,
                b"nonsense",
            ),
            x509.Attribute(
                x509.oid.AttributeOID.UNSTRUCTURED_NAME,
                b"montessori",
            ),
            x509.Attribute(
                x509.ObjectIdentifier("2.999.2"),
                b"meaningless",
            ),
            x509.Attribute(
                x509.ObjectIdentifier("2.999.1"),
                b"meaningless",
            ),
        ]
        attrs = x509.Attributes(attr_list)
        assert len(attrs) == 4
        assert list(attrs) == attr_list
        assert attrs[-1] == attrs[3]
        assert attrs[0:3:2] == [attrs[0], attrs[2]]

    def test_get_attribute_not_found(self):
        attrs = x509.Attributes([])
        with pytest.raises(x509.AttributeNotFound) as exc:
            attrs.get_attribute_for_oid(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD
            )
        assert exc.value.oid == x509.oid.AttributeOID.CHALLENGE_PASSWORD

    def test_repr(self):
        attrs = x509.Attributes(
            [
                x509.Attribute(
                    x509.oid.AttributeOID.CHALLENGE_PASSWORD,
                    b"nonsense",
                ),
            ]
        )
        assert repr(attrs) == (
            "<Attributes([<Attribute(oid=<ObjectIdentifier(oid=1.2.840.11354"
            "9.1.9.7, name=challengePassword)>, value=b'nonsense')>])>"
        )


class TestRequestAttributes:
    def test_get_attribute_for_oid_challenge(self):
        request = _load_cert(
            os.path.join("x509", "requests", "challenge.pem"),
            x509.load_pem_x509_csr,
        )

        assert request.attributes.get_attribute_for_oid(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD
        ) == x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"challenge me!",
        )

    def test_get_attribute_for_oid_multiple(self):
        request = _load_cert(
            os.path.join("x509", "requests", "challenge-unstructured.pem"),
            x509.load_pem_x509_csr,
        )

        assert request.attributes.get_attribute_for_oid(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD
        ) == x509.Attribute(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD,
            b"beauty",
        )

        assert request.attributes.get_attribute_for_oid(
            x509.oid.AttributeOID.UNSTRUCTURED_NAME
        ) == x509.Attribute(
            x509.oid.AttributeOID.UNSTRUCTURED_NAME,
            b"an unstructured field",
        )

    def test_unsupported_asn1_type_in_attribute(self):
        request = _load_cert(
            os.path.join("x509", "requests", "challenge-invalid.der"),
            x509.load_der_x509_csr,
        )

        # supported in the new path where we just store the type and
        # return raw bytes
        attr = request.attributes.get_attribute_for_oid(
            x509.oid.AttributeOID.CHALLENGE_PASSWORD
        )
        assert attr._type == 2

    def test_long_form_asn1_tag_in_attribute(self):
        request = _load_cert(
            os.path.join("x509", "requests", "long-form-attribute.pem"),
            x509.load_pem_x509_csr,
        )
        with pytest.raises(ValueError, match="Long-form"):
            request.attributes

    def test_challenge_multivalued(self):
        """
        We only support single-valued SETs in our X509 request attributes
        """
        request = _load_cert(
            os.path.join("x509", "requests", "challenge-multi-valued.der"),
            x509.load_der_x509_csr,
        )
        with pytest.raises(ValueError, match="Only single-valued"):
            request.attributes

    def test_no_challenge_password(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        with pytest.raises(x509.AttributeNotFound) as exc:
            request.attributes.get_attribute_for_oid(
                x509.oid.AttributeOID.CHALLENGE_PASSWORD
            )
        assert exc.value.oid == x509.oid.AttributeOID.CHALLENGE_PASSWORD

    def test_no_attributes(self):
        request = _load_cert(
            os.path.join("x509", "requests", "rsa_sha256.pem"),
            x509.load_pem_x509_csr,
        )
        assert len(request.attributes) == 0

    def test_zero_element_attribute(self):
        request = _load_cert(
            os.path.join("x509", "requests", "zero-element-attribute.pem"),
            x509.load_pem_x509_csr,
        )
        with pytest.raises(ValueError, match="Only single-valued"):
            request.attributes


def test_load_pem_x509_certificates():
    with pytest.raises(ValueError):
        x509.load_pem_x509_certificates(b"")

    certs = load_vectors_from_file(
        filename=os.path.join("x509", "cryptography.io.chain.pem"),
        loader=lambda pemfile: x509.load_pem_x509_certificates(pemfile.read()),
        mode="rb",
    )
    assert len(certs) == 2
    assert certs[0].serial_number == 16160
    assert certs[1].serial_number == 146039

    certs = load_vectors_from_file(
        filename=os.path.join(
            "x509", "cryptography.io.chain_with_garbage.pem"
        ),
        loader=lambda pemfile: x509.load_pem_x509_certificates(pemfile.read()),
        mode="rb",
    )
    assert len(certs) == 2
    assert certs[0].serial_number == 16160
    assert certs[1].serial_number == 146039