diff --git a/CHANGELOG.md b/CHANGELOG.md
index a040aca1a7..b7a53e1be7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,14 @@
 
 <!-- insert new changelog below this comment -->
 
+## [Unreleased]
+
+### Added
+
+- feat(cli): opt-in launch warning when a newer spec-kit release is available; enable with `SPECIFY_ENABLE_UPDATE_CHECK=1` (or `true`/`yes`/`on`), cached for 24h, and suppressed in non-interactive shells and when `CI` is set (#1320)
+- fix(cli): cache update-check failures so transient outages don't trigger a network call on every CLI invocation (#1320)
+- refactor(cli): move update-check helpers into `_version.py` and reuse the existing `_get_installed_version` / `_fetch_latest_release_tag` / `_is_newer` primitives from #2550 (#1320)
+
 ## [0.8.13] - 2026-05-21
 
 ### Changed
diff --git a/docs/installation.md b/docs/installation.md
index b3c25ce469..be295d5eb5 100644
--- a/docs/installation.md
+++ b/docs/installation.md
@@ -99,6 +99,23 @@ Scripts are installed into a variant subdirectory matching the chosen script typ
 - `.specify/scripts/bash/` — contains `.sh` scripts (default on Linux/macOS)
 - `.specify/scripts/powershell/` — contains `.ps1` scripts (default on Windows)
 
+### Update Notifications
+
+`specify` can check once per 24 hours whether a newer release is available on GitHub and print an upgrade hint. This is **opt-in**: the check is off by default because air-gapped and network-constrained environments cannot reach GitHub.
+
+To enable it, set:
+
+```bash
+export SPECIFY_ENABLE_UPDATE_CHECK=1   # or true / yes / on
+```
+
+Even when enabled, the check stays silent when:
+
+- stdout is not a TTY (piped output, redirected to a file, etc.)
+- the `CI` environment variable is set
+
+Network failures and rate-limit responses are swallowed — the check never fails the command you ran, though a cache miss may add a small startup delay (bounded by a 5-second fetch timeout) while contacting GitHub. Failures are also cached for the same 24h window, so a transient outage or block won't cause the CLI to retry on every invocation.
+
 ## Troubleshooting
 
 ### Enterprise / Air-Gapped Installation
diff --git a/src/specify_cli/__init__.py b/src/specify_cli/__init__.py
index c0bdbaabe3..e875574055 100644
--- a/src/specify_cli/__init__.py
+++ b/src/specify_cli/__init__.py
@@ -97,6 +97,7 @@
     self_app as _self_app,
     self_check as self_check,
     self_upgrade as self_upgrade,
+    _check_for_updates,
 )
 
 def _build_agent_config() -> dict[str, dict[str, Any]]:
@@ -200,6 +201,16 @@ def callback(
         show_banner()
         console.print(Align.center("[dim]Run 'specify --help' for usage information[/dim]"))
         console.print()
+    # Addresses #1320: nudge users running outdated CLIs. The `version` subcommand
+    # already surfaces the version, so skip there to avoid double-printing; also
+    # skip help invocations. Runs on bare `specify` too so the banner launch
+    # benefits from the nudge when the user has opted in.
+    if (
+        ctx.invoked_subcommand != "version"
+        and "--help" not in sys.argv
+        and "-h" not in sys.argv
+    ):
+        _check_for_updates()
 
 def _refresh_shared_templates(
     project_path: Path,
diff --git a/src/specify_cli/_version.py b/src/specify_cli/_version.py
index 0a52ac7e80..7152856df2 100644
--- a/src/specify_cli/_version.py
+++ b/src/specify_cli/_version.py
@@ -10,7 +10,11 @@
 from __future__ import annotations
 
 import json
+import os
+import sys
+import time
 import urllib.error
+from pathlib import Path
 
 import typer
 from packaging.version import InvalidVersion, Version
@@ -171,3 +175,125 @@ def self_upgrade() -> None:
     console.print("specify self upgrade is not implemented yet.")
     console.print("Run 'specify self check' to see whether a newer release is available.")
     console.print("Actual self-upgrade is planned as follow-up work.")
+
+
+# ===== Opt-in startup update check (addresses #1320) =====
+#
+# Silent companion to `specify self check`: when SPECIFY_ENABLE_UPDATE_CHECK=1
+# is set in an interactive non-CI shell, the top-level Typer callback prints
+# upgrade guidance if a newer release is available. Result is cached for 24h in
+# the platform user-cache dir; cache misses are written even on fetch failure
+# (`latest=null`) so a transient outage doesn't trigger a network call on every
+# CLI invocation. Best-effort: every error path swallows the exception so the
+# helper never fails the command the user actually invoked, though cache misses
+# may add a bounded startup delay while contacting GitHub.
+
+_UPDATE_CHECK_CACHE_TTL_SECONDS = 24 * 60 * 60
+
+
+def _update_check_cache_path() -> Path | None:
+    try:
+        from platformdirs import user_cache_dir
+        return Path(user_cache_dir("specify-cli")) / "version_check.json"
+    except Exception:
+        return None
+
+
+def _read_update_check_cache(path: Path) -> dict | None:
+    try:
+        if not path.exists():
+            return None
+        data = json.loads(path.read_text(encoding="utf-8"))
+        checked_at = float(data.get("checked_at", 0))
+        latest = data.get("latest")
+        if latest is not None and not isinstance(latest, str):
+            return None
+        if time.time() - checked_at > _UPDATE_CHECK_CACHE_TTL_SECONDS:
+            return None
+        return data
+    except Exception:
+        return None
+
+
+def _write_update_check_cache(path: Path, latest: str | None) -> None:
+    try:
+        path.parent.mkdir(parents=True, exist_ok=True)
+        path.write_text(
+            json.dumps({"checked_at": time.time(), "latest": latest}),
+            encoding="utf-8",
+        )
+    except Exception:
+        # Cache write failures are non-fatal.
+        pass
+
+
+def _should_skip_update_check() -> bool:
+    # Opt-in only: air-gapped / network-constrained environments cannot reach
+    # GitHub, so the check is off by default.
+    if os.environ.get("SPECIFY_ENABLE_UPDATE_CHECK", "").strip().lower() not in ("1", "true", "yes", "on"):
+        return True
+    # Belt-and-suspenders: even when opted in, suppress in CI and when the
+    # caller isn't a TTY so we don't dirty machine-readable output.
+    if os.environ.get("CI"):
+        return True
+    try:
+        if not sys.stdout.isatty():
+            return True
+    except Exception:
+        return True
+    return False
+
+
+def _check_for_updates() -> None:
+    """Print upgrade guidance when a newer spec-kit release is available.
+
+    Fully best-effort — any error (offline, rate-limited, parse failure) is
+    swallowed so the command the user actually invoked is never failed.
+    """
+    if _should_skip_update_check():
+        return
+    try:
+        current = _get_installed_version()
+        if current == "unknown":
+            return
+
+        cache_path = _update_check_cache_path()
+        cached = _read_update_check_cache(cache_path) if cache_path is not None else None
+        if cached is not None:
+            # Fresh cache hit — may be a positive (`latest=v…`) or
+            # negative (`latest=null`) entry; either way, no fetch.
+            latest_tag = cached.get("latest")
+        else:
+            try:
+                latest_tag, _reason = _fetch_latest_release_tag()
+            except Exception:
+                if cache_path is not None:
+                    # Cache malformed/unexpected fetch failures too, so they
+                    # don't trigger a network call on every CLI invocation.
+                    _write_update_check_cache(cache_path, None)
+                return
+            if cache_path is not None:
+                # Cache the attempt even on failure so transient outages
+                # don't trigger a network call on every CLI invocation.
+                _write_update_check_cache(cache_path, latest_tag)
+
+        if not latest_tag:
+            return
+        latest_display = _normalize_tag(latest_tag)
+        if not _is_newer(latest_display, current):
+            return
+
+        console.print(
+            f"[yellow]⚠  A new spec-kit version is available: "
+            f"v{latest_display} (you have v{current})[/yellow]"
+        )
+        console.print(
+            f"[dim]   Upgrade: uv tool install specify-cli --force "
+            f"--from git+https://github.com/github/spec-kit.git@{latest_tag}[/dim]"
+        )
+        console.print(
+            "[dim]   (unset SPECIFY_ENABLE_UPDATE_CHECK to disable this check)[/dim]"
+        )
+    except Exception:
+        # Update check must never surface an error to the user.
+        return
diff --git a/tests/test_update_check.py b/tests/test_update_check.py
new file mode 100644
index 0000000000..1d9e282af1
--- /dev/null
+++ b/tests/test_update_check.py
@@ -0,0 +1,286 @@
+"""Tests for the update-check helper in specify_cli._version.
+
+Covers issue https://github.com/github/spec-kit/issues/1320 — the CLI should
+nudge users who are running outdated releases toward an upgrade, without
+failing any command when offline or rate-limited.
+"""
+
+import json
+import time
+from io import StringIO
+
+from specify_cli._version import (
+    _check_for_updates,
+    _read_update_check_cache,
+    _write_update_check_cache,
+)
+
+
+
+class TestCache:
+    def test_fresh_cache_is_returned(self, tmp_path):
+        cache_file = tmp_path / "version_check.json"
+        cache_file.write_text(json.dumps({"checked_at": time.time(), "latest": "v0.7.0"}))
+        data = _read_update_check_cache(cache_file)
+        assert data is not None
+        assert data["latest"] == "v0.7.0"
+
+    def test_stale_cache_is_ignored(self, tmp_path):
+        cache_file = tmp_path / "version_check.json"
+        very_old = time.time() - (48 * 60 * 60)
+        cache_file.write_text(json.dumps({"checked_at": very_old, "latest": "v0.5.0"}))
+        assert _read_update_check_cache(cache_file) is None
+
+    def test_missing_cache_returns_none(self, tmp_path):
+        assert _read_update_check_cache(tmp_path / "missing.json") is None
+
+    def test_corrupt_cache_returns_none(self, tmp_path):
+        cache_file = tmp_path / "version_check.json"
+        cache_file.write_text("{not json")
+        assert _read_update_check_cache(cache_file) is None
+
+    def test_invalid_latest_cache_type_returns_none(self, tmp_path):
+        cache_file = tmp_path / "version_check.json"
+        cache_file.write_text(json.dumps({"checked_at": time.time(), "latest": ["v0.7.0"]}))
+        assert _read_update_check_cache(cache_file) is None
+
+    def test_write_round_trips(self, tmp_path):
+        cache_file = tmp_path / "nested" / "version_check.json"
+        _write_update_check_cache(cache_file, "v0.9.9")
+        assert cache_file.exists()
+        data = json.loads(cache_file.read_text())
+        assert data["latest"] == "v0.9.9"
+        assert float(data["checked_at"]) <= time.time()
+
+    def test_write_round_trips_negative_entry(self, tmp_path):
+        cache_file = tmp_path / "nested" / "version_check.json"
+        _write_update_check_cache(cache_file, None)
+        assert cache_file.exists()
+        data = json.loads(cache_file.read_text())
+        assert data["latest"] is None
+        assert float(data["checked_at"]) <= time.time()
+
+
+
+class TestCheckForUpdates:
+    """End-to-end-ish checks on `_check_for_updates` with skip conditions patched off."""
+
+    def _run_and_capture(self, monkeypatch) -> str:
+        """Force the skip-guard off so the helper runs, then capture console output."""
+        # Guard returns False → helper proceeds.
+        monkeypatch.setattr("specify_cli._version._should_skip_update_check", lambda: False)
+        buf = StringIO()
+        import specify_cli._version
+        from rich.console import Console
+        captured = Console(file=buf, force_terminal=False, width=200)
+        monkeypatch.setattr(specify_cli._version, "console", captured)
+        _check_for_updates()
+        return buf.getvalue()
+
+    def test_prints_warning_when_newer_release_available(self, monkeypatch, tmp_path):
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", lambda: ("v0.7.0", None))
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert "new spec-kit version is available" in out
+        assert "v0.7.0" in out
+        assert "v0.6.2" in out
+        assert "uv tool install specify-cli" in out
+
+    def test_upgrade_command_uses_exact_release_tag(self, monkeypatch, tmp_path):
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", lambda: ("0.7.0", None))
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert "git+https://github.com/github/spec-kit.git@0.7.0" in out
+        assert "git+https://github.com/github/spec-kit.git@v0.7.0" not in out
+
+    def test_no_output_when_up_to_date(self, monkeypatch, tmp_path):
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.7.0")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", lambda: ("v0.7.0", None))
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert out == ""
+
+    def test_uses_cache_when_fresh(self, monkeypatch, tmp_path):
+        cache_file = tmp_path / "vc.json"
+        cache_file.write_text(json.dumps({"checked_at": time.time(), "latest": "v0.7.0"}))
+
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr("specify_cli._version._update_check_cache_path", lambda: cache_file)
+
+        call_counter = {"n": 0}
+
+        def _should_not_be_called() -> tuple[str | None, str | None]:
+            call_counter["n"] += 1
+            return (None, None)
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _should_not_be_called)
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert call_counter["n"] == 0
+        assert "v0.7.0" in out
+
+    def test_network_failure_is_silent(self, monkeypatch, tmp_path):
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", lambda: (None, "offline or timeout"))
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert out == ""
+
+    def test_network_failure_writes_negative_cache(self, monkeypatch, tmp_path):
+        cache_file = tmp_path / "vc.json"
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr("specify_cli._version._update_check_cache_path", lambda: cache_file)
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", lambda: (None, "offline or timeout"))
+
+        self._run_and_capture(monkeypatch)
+
+        assert cache_file.exists()
+        data = json.loads(cache_file.read_text())
+        assert data["latest"] is None
+        assert time.time() - float(data["checked_at"]) < 5
+
+    def test_fetch_exception_writes_negative_cache(self, monkeypatch, tmp_path):
+        cache_file = tmp_path / "vc.json"
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr("specify_cli._version._update_check_cache_path", lambda: cache_file)
+
+        def _fetch_raises() -> tuple[str | None, str | None]:
+            raise ValueError("GitHub API response missing valid tag_name")
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _fetch_raises)
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert out == ""
+        assert cache_file.exists()
+        data = json.loads(cache_file.read_text())
+        assert data["latest"] is None
+        assert time.time() - float(data["checked_at"]) < 5
+
+    def test_negative_cache_skips_fetch_within_ttl(self, monkeypatch, tmp_path):
+        cache_file = tmp_path / "vc.json"
+        cache_file.write_text(json.dumps({"checked_at": time.time(), "latest": None}))
+
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr("specify_cli._version._update_check_cache_path", lambda: cache_file)
+
+        call_counter = {"n": 0}
+
+        def _should_not_be_called() -> tuple[str | None, str | None]:
+            call_counter["n"] += 1
+            return (None, None)
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _should_not_be_called)
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert call_counter["n"] == 0
+        assert out == ""
+
+    def test_invalid_latest_cache_type_is_treated_as_miss(self, monkeypatch, tmp_path):
+        cache_file = tmp_path / "vc.json"
+        cache_file.write_text(json.dumps({"checked_at": time.time(), "latest": ["v0.7.0"]}))
+
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.6.2")
+        monkeypatch.setattr("specify_cli._version._update_check_cache_path", lambda: cache_file)
+
+        call_counter = {"n": 0}
+
+        def _fetch() -> tuple[str | None, str | None]:
+            call_counter["n"] += 1
+            return ("v0.7.0", None)
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _fetch)
+
+        out = self._run_and_capture(monkeypatch)
+
+        assert call_counter["n"] == 1
+        assert "v0.7.0" in out
+
+    def test_opt_in_default_off_short_circuits(self, monkeypatch, tmp_path):
+        """Without SPECIFY_ENABLE_UPDATE_CHECK the helper must not hit the network."""
+        monkeypatch.delenv("SPECIFY_ENABLE_UPDATE_CHECK", raising=False)
+
+        fetched = {"called": False}
+
+        def _fetch():
+            fetched["called"] = True
+            return ("v99.0.0", None)
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _fetch)
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.0.1")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+
+        _check_for_updates()
+
+        assert fetched["called"] is False
+
+    def test_opt_in_env_var_allows_check(self, monkeypatch, tmp_path):
+        """With SPECIFY_ENABLE_UPDATE_CHECK=1 and a TTY, the helper proceeds."""
+        monkeypatch.setenv("SPECIFY_ENABLE_UPDATE_CHECK", "1")
+        monkeypatch.delenv("CI", raising=False)
+        monkeypatch.setattr("sys.stdout.isatty", lambda: True)
+
+        fetched = {"called": False}
+
+        def _fetch():
+            fetched["called"] = True
+            return ("v99.0.0", None)
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _fetch)
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.0.1")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+
+        _check_for_updates()
+
+        assert fetched["called"] is True
+
+    def test_ci_suppresses_even_when_opted_in(self, monkeypatch, tmp_path):
+        """Belt-and-suspenders: CI=1 wins over the opt-in flag.
+
+        Pin isatty()=True so this test fails if the CI guard is removed —
+        otherwise pytest's stdout capture makes isatty False and the TTY
+        guard alone would suppress the fetch, masking a regression.
+        """
+        monkeypatch.setenv("SPECIFY_ENABLE_UPDATE_CHECK", "1")
+        monkeypatch.setenv("CI", "1")
+        monkeypatch.setattr("sys.stdout.isatty", lambda: True)
+
+        fetched = {"called": False}
+
+        def _fetch():
+            fetched["called"] = True
+            return ("v99.0.0", None)
+
+        monkeypatch.setattr("specify_cli._version._fetch_latest_release_tag", _fetch)
+        monkeypatch.setattr("specify_cli._version._get_installed_version", lambda: "0.0.1")
+        monkeypatch.setattr(
+            "specify_cli._version._update_check_cache_path", lambda: tmp_path / "vc.json"
+        )
+
+        _check_for_updates()
+
+        assert fetched["called"] is False