diff --git a/app/md-exports/[...path]/route.test.ts b/app/md-exports/[...path]/route.test.ts
new file mode 100644
index 0000000000000..23894ae7cae8c
--- /dev/null
+++ b/app/md-exports/[...path]/route.test.ts
@@ -0,0 +1,132 @@
+import {readFile} from 'node:fs/promises';
+
+import {beforeEach, describe, expect, it, vi} from 'vitest';
+
+vi.mock('node:fs/promises', () => ({
+  readFile: vi.fn(),
+}));
+
+const SAMPLE_DOCTREE = {
+  path: '',
+  slug: '',
+  frontmatter: {title: 'Home'},
+  children: [
+    {
+      path: 'platforms',
+      slug: 'platforms',
+      frontmatter: {title: 'Platforms'},
+      children: [
+        {
+          path: 'platforms/javascript',
+          slug: 'javascript',
+          frontmatter: {title: 'Browser JavaScript'},
+          children: [
+            {
+              path: 'platforms/javascript/install',
+              slug: 'install',
+              frontmatter: {title: 'Installation Methods'},
+            },
+            {
+              path: 'platforms/javascript/usage',
+              slug: 'usage',
+              frontmatter: {title: 'Capturing Errors'},
+            },
+            {
+              path: 'platforms/javascript/tracing',
+              slug: 'tracing',
+              frontmatter: {title: 'Set Up Tracing'},
+            },
+          ],
+        },
+        {
+          path: 'platforms/python',
+          slug: 'python',
+          frontmatter: {title: 'Python'},
+          children: [],
+        },
+      ],
+    },
+  ],
+};
+
+describe('md-exports 404 catch-all route', () => {
+  beforeEach(() => {
+    vi.resetModules();
+    vi.mocked(readFile).mockResolvedValue(JSON.stringify(SAMPLE_DOCTREE));
+  });
+
+  async function callRoute(pathSegments: string[]) {
+    const {GET} = await import('./route');
+    const request = new Request('https://docs.sentry.io/test');
+    return GET(request, {params: Promise.resolve({path: pathSegments})});
+  }
+
+  it('returns 404 status', async () => {
+    const res = await callRoute(['platforms', 'javascript', 'ai-monitoring.md']);
+    expect(res.status).toBe(404);
+  });
+
+  it('returns text/markdown content type', async () => {
+    const res = await callRoute(['platforms', 'javascript', 'ai-monitoring.md']);
+    expect(res.headers.get('Content-Type')).toBe('text/markdown; charset=utf-8');
+  });
+
+  it('includes the requested path in the body', async () => {
+    const res = await callRoute(['platforms', 'javascript', 'ai-monitoring.md']);
+    const body = await res.text();
+    expect(body).toContain('/platforms/javascript/ai-monitoring');
+  });
+
+  it('includes sibling pages from the parent section', async () => {
+    const res = await callRoute(['platforms', 'javascript', 'ai-monitoring.md']);
+    const body = await res.text();
+    expect(body).toContain('Installation Methods');
+    expect(body).toContain('Capturing Errors');
+    expect(body).toContain('Set Up Tracing');
+    expect(body).toContain('Pages in Browser JavaScript');
+  });
+
+  it('includes navigation links to llms.txt and index.md', async () => {
+    const res = await callRoute(['platforms', 'javascript', 'ai-monitoring.md']);
+    const body = await res.text();
+    expect(body).toContain('llms.txt');
+    expect(body).toContain('index.md');
+    expect(body).toContain('platforms.md');
+  });
+
+  it('walks up the tree when the immediate parent does not exist', async () => {
+    const res = await callRoute([
+      'platforms',
+      'javascript',
+      'nonexistent',
+      'deep',
+      'path.md',
+    ]);
+    const body = await res.text();
+    expect(body).toContain('Pages in Browser JavaScript');
+  });
+
+  it('falls back to top-level sections when nothing matches', async () => {
+    const res = await callRoute(['completely', 'unknown', 'path.md']);
+    const body = await res.text();
+    expect(body).not.toContain('Pages in');
+    expect(body).toContain('Find what you need');
+  });
+
+  it('handles doctree load failure gracefully', async () => {
+    vi.mocked(readFile).mockRejectedValue(new Error('file not found'));
+    const res = await callRoute(['platforms', 'javascript', 'foo.md']);
+    const body = await res.text();
+    expect(res.status).toBe(404);
+    expect(body).toContain('Page Not Found');
+    expect(body).toContain('llms.txt');
+  });
+
+  it('includes YAML frontmatter', async () => {
+    const res = await callRoute(['platforms', 'javascript', 'foo.md']);
+    const body = await res.text();
+    expect(body).toMatch(/^---\n/);
+    expect(body).toContain('title: "Page Not Found"');
+    expect(body).toContain('url: "https://docs.sentry.io/platforms/javascript/foo"');
+  });
+});
diff --git a/app/md-exports/[...path]/route.ts b/app/md-exports/[...path]/route.ts
new file mode 100644
index 0000000000000..c8e098b875151
--- /dev/null
+++ b/app/md-exports/[...path]/route.ts
@@ -0,0 +1,136 @@
+import {readFile} from 'node:fs/promises';
+import {join} from 'node:path';
+
+import {isDeveloperDocs} from 'sentry-docs/isDeveloperDocs';
+
+interface DocTreeNode {
+  path: string;
+  slug: string;
+  frontmatter: {title?: string; description?: string};
+  children?: DocTreeNode[];
+}
+
+const BASE_URL = isDeveloperDocs
+  ? 'https://develop.sentry.dev'
+  : 'https://docs.sentry.io';
+
+let cachedDocTree: DocTreeNode | null = null;
+
+async function getDocTree(): Promise<DocTreeNode> {
+  if (cachedDocTree) {
+    return cachedDocTree;
+  }
+  const filename = isDeveloperDocs ? 'doctree-dev.json' : 'doctree.json';
+  const treePath = join(process.cwd(), 'public', filename);
+  const raw = await readFile(treePath, 'utf-8');
+  cachedDocTree = JSON.parse(raw) as DocTreeNode;
+  return cachedDocTree;
+}
+
+function findNode(node: DocTreeNode, targetPath: string): DocTreeNode | null {
+  if (node.path === targetPath) {
+    return node;
+  }
+  for (const child of node.children ?? []) {
+    const found = findNode(child, targetPath);
+    if (found) {
+      return found;
+    }
+  }
+  return null;
+}
+
+function findClosestAncestor(
+  tree: DocTreeNode,
+  pathSegments: string[]
+): DocTreeNode | null {
+  for (let i = pathSegments.length; i > 0; i--) {
+    const candidatePath = pathSegments.slice(0, i).join('/');
+    const node = findNode(tree, candidatePath);
+    if (node) {
+      return node;
+    }
+  }
+  return null;
+}
+
+function renderSiblingList(siblings: DocTreeNode[], baseUrl: string): string {
+  return siblings
+    .slice(0, 15)
+    .map(s => {
+      const title = s.frontmatter?.title || s.slug;
+      return `- [${title}](${baseUrl}/${s.path}.md)`;
+    })
+    .join('\n');
+}
+
+export async function GET(
+  _request: Request,
+  {params}: {params: Promise<{path: string[]}>}
+) {
+  const {path: pathSegments} = await params;
+  const requestedPath = pathSegments.join('/').replace(/\.md$/, '');
+
+  let body: string;
+
+  try {
+    const tree = await getDocTree();
+    const ancestor = findClosestAncestor(tree, requestedPath.split('/'));
+
+    const lines: string[] = [
+      '---',
+      `title: "Page Not Found"`,
+      `url: "${BASE_URL}/${requestedPath}"`,
+      '---',
+      '',
+      '# Page Not Found',
+      '',
+      `The page \`/${requestedPath}\` does not exist.`,
+      '',
+    ];
+
+    if (ancestor && ancestor.children?.length) {
+      const ancestorTitle =
+        ancestor.frontmatter?.title || ancestor.slug || 'this section';
+      lines.push(`## Pages in ${ancestorTitle}`);
+      lines.push('');
+      lines.push(renderSiblingList(ancestor.children, BASE_URL));
+      lines.push('');
+    }
+
+    lines.push('## Find what you need');
+    lines.push('');
+    lines.push(`- [Site index](${BASE_URL}/llms.txt) — LLM-optimized page listing`);
+    lines.push(`- [Documentation root](${BASE_URL}/index.md) — full docs overview`);
+    lines.push(`- [Platforms](${BASE_URL}/platforms.md) — all SDK platforms`);
+    lines.push('');
+
+    body = lines.join('\n');
+  } catch {
+    body = [
+      '---',
+      `title: "Page Not Found"`,
+      `url: "${BASE_URL}/${requestedPath}"`,
+      '---',
+      '',
+      '# Page Not Found',
+      '',
+      `The page \`/${requestedPath}\` does not exist.`,
+      '',
+      '## Find what you need',
+      '',
+      `- [Site index](${BASE_URL}/llms.txt) — LLM-optimized page listing`,
+      `- [Documentation root](${BASE_URL}/index.md) — full docs overview`,
+      `- [Platforms](${BASE_URL}/platforms.md) — all SDK platforms`,
+      '',
+    ].join('\n');
+  }
+
+  return new Response(body, {
+    status: 404,
+    headers: {
+      'Content-Type': 'text/markdown; charset=utf-8',
+      'Cache-Control': 'public, max-age=300',
+    },
+  });
+}
diff --git a/next.config.ts b/next.config.ts
index 8e2c428a61ed6..4662d206569fe 100644
--- a/next.config.ts
+++ b/next.config.ts
@@ -75,6 +75,7 @@ const outputFileTracingIncludes = process.env.NEXT_PUBLIC_DEVELOPER_DOCS
   ? {
       '/platform-redirect': ['public/doctree-dev.json'],
       '\\[\\[\\.\\.\\.path\\]\\]': ['public/doctree-dev.json'],
+      '/md-exports/\\[\\.\\.\\.path\\]': ['public/doctree-dev.json'],
       'sitemap.xml': ['public/doctree-dev.json'],
     }
   : {
@@ -84,6 +85,7 @@ const outputFileTracingIncludes = process.env.NEXT_PUBLIC_DEVELOPER_DOCS
         'docs/changelog.mdx',
         'docs/platforms/index.mdx',
       ],
+      '/md-exports/\\[\\.\\.\\.path\\]': ['public/doctree.json'],
       'sitemap.xml': ['public/doctree.json'],
     };