diff --git a/.github/pr-assets/ai-guides-structured-outputs-error.png b/.github/pr-assets/ai-guides-structured-outputs-error.png
new file mode 100644
index 000000000..1947a27c8
Binary files /dev/null and b/.github/pr-assets/ai-guides-structured-outputs-error.png differ
diff --git a/src/routes/$libraryId/$version.docs.$.tsx b/src/routes/$libraryId/$version.docs.$.tsx
index ee525cec5..5906dac26 100644
--- a/src/routes/$libraryId/$version.docs.$.tsx
+++ b/src/routes/$libraryId/$version.docs.$.tsx
@@ -1,5 +1,6 @@
 import { seo } from '~/utils/seo'
 import { Doc } from '~/components/Doc'
+import { isDocsNotFoundError } from '~/utils/docs-errors'
 import { loadDocsPage, resolveDocsRedirect } from '~/utils/docs'
 import { findLibrary, getBranch, getLibrary } from '~/libraries'
 import { DocContainer } from '~/components/DocContainer'
@@ -36,6 +37,7 @@ export const Route = createFileRoute('/$libraryId/$version/docs/$')({
       })
     } catch (error) {
       const isNotFoundError =
+        isDocsNotFoundError(error) ||
         isNotFound(error) ||
         (error && typeof error === 'object' && 'isNotFound' in error)
 
diff --git a/src/routes/$libraryId/$version.docs.framework.$framework.$.tsx b/src/routes/$libraryId/$version.docs.framework.$framework.$.tsx
index b0eb34fb6..b810f961f 100644
--- a/src/routes/$libraryId/$version.docs.framework.$framework.$.tsx
+++ b/src/routes/$libraryId/$version.docs.framework.$framework.$.tsx
@@ -7,6 +7,7 @@ import {
 } from '@tanstack/react-router'
 import { seo } from '~/utils/seo'
 import { Doc } from '~/components/Doc'
+import { isDocsNotFoundError } from '~/utils/docs-errors'
 import { loadDocsPage, resolveDocsRedirect } from '~/utils/docs'
 import { getBranch, getLibrary } from '~/libraries'
 import { capitalize } from '~/utils/utils'
@@ -36,6 +37,7 @@ export const Route = createFileRoute(
       // This handles cases like switching frameworks where the same doc path doesn't exist
       // Check both isNotFound() and the serialized form from server functions
       const isNotFoundError =
+        isDocsNotFoundError(error) ||
         isNotFound(error) ||
         (error && typeof error === 'object' && 'isNotFound' in error)
 
diff --git a/src/routes/$libraryId/$version.docs.framework.$framework.{$}[.]md.tsx b/src/routes/$libraryId/$version.docs.framework.$framework.{$}[.]md.tsx
index fe302cbe8..c49d1a3f4 100644
--- a/src/routes/$libraryId/$version.docs.framework.$framework.{$}[.]md.tsx
+++ b/src/routes/$libraryId/$version.docs.framework.$framework.{$}[.]md.tsx
@@ -1,6 +1,7 @@
 import { findLibrary, getBranch } from '~/libraries'
-import { loadDocs } from '~/utils/docs'
-import { notFound, createFileRoute } from '@tanstack/react-router'
+import { isDocsNotFoundError } from '~/utils/docs-errors'
+import { loadDocs, resolveDocsRedirect } from '~/utils/docs'
+import { notFound, redirect, createFileRoute } from '@tanstack/react-router'
 import { filterFrameworkContent } from '~/utils/markdown/filterFrameworkContent'
 import { getPackageManager } from '~/utils/markdown/installCommand'
 
@@ -34,12 +35,41 @@ export const Route = createFileRoute(
 
         const root = library.docsRoot || 'docs'
 
-        const doc = await loadDocs({
-          repo: library.repo,
-          branch: getBranch(library, version),
-          docsRoot: root,
-          docsPath: `framework/${framework}/${docsPath}`,
-        })
+        let doc
+
+        try {
+          doc = await loadDocs({
+            repo: library.repo,
+            branch: getBranch(library, version),
+            docsRoot: root,
+            docsPath: `framework/${framework}/${docsPath}`,
+          })
+        } catch (error) {
+          if (isDocsNotFoundError(error)) {
+            const redirectPath = await resolveDocsRedirect({
+              repo: library.repo,
+              branch: getBranch(library, version),
+              docsRoot: root,
+              docsPaths: docsPath
+                ? [
+                    `framework/${framework}/${docsPath}`,
+                    `${framework}/${docsPath}`,
+                  ]
+                : [],
+            })
+
+            if (redirectPath !== null) {
+              throw redirect({
+                href: `/${libraryId}/${version}/docs/${redirectPath}.md`,
+                statusCode: 308,
+              })
+            }
+
+            throw notFound()
+          }
+
+          throw error
+        }
 
         // Filter framework-specific content using framework from URL path
         const filteredContent = filterFrameworkContent(doc.content, {
diff --git a/src/routes/$libraryId/$version.docs.{$}[.]md.tsx b/src/routes/$libraryId/$version.docs.{$}[.]md.tsx
index 5ec537ade..a37af6db7 100644
--- a/src/routes/$libraryId/$version.docs.{$}[.]md.tsx
+++ b/src/routes/$libraryId/$version.docs.{$}[.]md.tsx
@@ -1,6 +1,7 @@
-import { createFileRoute } from '@tanstack/react-router'
+import { createFileRoute, notFound, redirect } from '@tanstack/react-router'
 import { getBranch, getLibrary, type LibraryId } from '~/libraries'
-import { loadDocs } from '~/utils/docs'
+import { isDocsNotFoundError } from '~/utils/docs-errors'
+import { loadDocs, resolveDocsRedirect } from '~/utils/docs'
 import { filterFrameworkContent } from '~/utils/markdown/filterFrameworkContent'
 import { getPackageManager } from '~/utils/markdown/installCommand'
 
@@ -23,12 +24,36 @@ export const Route = createFileRoute('/$libraryId/$version/docs/{$}.md')({
         const library = getLibrary(libraryId as LibraryId)
         const root = library.docsRoot || 'docs'
 
-        const doc = await loadDocs({
-          repo: library.repo,
-          branch: getBranch(library, version),
-          docsRoot: root,
-          docsPath,
-        })
+        let doc
+
+        try {
+          doc = await loadDocs({
+            repo: library.repo,
+            branch: getBranch(library, version),
+            docsRoot: root,
+            docsPath,
+          })
+        } catch (error) {
+          if (isDocsNotFoundError(error)) {
+            const redirectPath = await resolveDocsRedirect({
+              repo: library.repo,
+              branch: getBranch(library, version),
+              docsRoot: root,
+              docsPaths: [docsPath],
+            })
+
+            if (redirectPath !== null) {
+              throw redirect({
+                href: `/${libraryId}/${version}/docs/${redirectPath}.md`,
+                statusCode: 308,
+              })
+            }
+
+            throw notFound()
+          }
+
+          throw error
+        }
 
         // Filter framework-specific content only if framework is explicitly specified
         const filteredContent = framework
diff --git a/src/utils/docs-errors.ts b/src/utils/docs-errors.ts
new file mode 100644
index 000000000..12ef42853
--- /dev/null
+++ b/src/utils/docs-errors.ts
@@ -0,0 +1,25 @@
+type DocsNotFoundError = Error & {
+  data: { message: string }
+  isDocsNotFound: true
+}
+
+export function createDocsNotFoundError(message = 'No doc was found here!') {
+  const error = new Error(message) as DocsNotFoundError
+
+  error.name = 'DocsNotFoundError'
+  error.data = { message }
+  error.isDocsNotFound = true
+
+  return error
+}
+
+export function isDocsNotFoundError(
+  error: unknown,
+): error is DocsNotFoundError {
+  return (
+    typeof error === 'object' &&
+    error !== null &&
+    'isDocsNotFound' in error &&
+    error.isDocsNotFound === true
+  )
+}
diff --git a/src/utils/docs.functions.ts b/src/utils/docs.functions.ts
index dbfeea200..9f0e1309b 100644
--- a/src/utils/docs.functions.ts
+++ b/src/utils/docs.functions.ts
@@ -1,4 +1,3 @@
-import { notFound } from '@tanstack/react-router'
 import { createServerFn } from '@tanstack/react-start'
 import { setResponseHeader } from '@tanstack/react-start/server'
 import removeMarkdown from 'remove-markdown'
@@ -9,6 +8,7 @@ import {
   fetchRepoFile,
   isRecoverableGitHubContentError,
 } from '~/utils/documents.server'
+import { createDocsNotFoundError } from './docs-errors'
 import { renderMarkdownToRsc } from './markdown'
 import { getCachedDocsArtifact } from './github-content-cache.server'
 import { buildRedirectManifest, type RedirectManifestEntry } from './redirects'
@@ -223,7 +223,7 @@ export const fetchDocs = createServerFn({ method: 'GET' })
     const file = await readRepoFileOrFallback(repo, branch, filePath)
 
     if (!file) {
-      throw notFound()
+      throw createDocsNotFoundError()
     }
 
     const frontMatter = extractFrontMatter(file)
@@ -267,7 +267,7 @@ export const fetchFile = createServerFn({ method: 'GET' })
     const file = await readRepoFileOrFallback(repo, branch, filePath)
 
     if (!file) {
-      throw notFound()
+      throw createDocsNotFoundError()
     }
 
     setDocsCacheHeaders('max-age=3600, stale-while-revalidate=3600, durable')
@@ -284,7 +284,7 @@ export const fetchRepoDirectoryContents = createServerFn({
     const githubContents = await fetchApiContents(repo, branch, startingPath)
 
     if (!githubContents) {
-      throw notFound()
+      throw createDocsNotFoundError()
     }
 
     setDocsCacheHeaders('max-age=3600, stale-while-revalidate=3600, durable')
diff --git a/src/utils/docs.ts b/src/utils/docs.ts
index 204f37813..833ff7989 100644
--- a/src/utils/docs.ts
+++ b/src/utils/docs.ts
@@ -1,4 +1,3 @@
-import { notFound } from '@tanstack/react-router'
 import {
   fetchDocs,
   fetchDocsPage,
@@ -7,6 +6,7 @@ import {
   fetchFile,
   fetchRepoDirectoryContents,
 } from './docs.functions'
+import { createDocsNotFoundError } from './docs-errors'
 import { removeLeadingSlash } from './utils'
 
 export const loadDocs = async ({
@@ -21,11 +21,7 @@ export const loadDocs = async ({
   docsPath: string
 }) => {
   if (!branch || !docsRoot || !docsPath) {
-    throw notFound({
-      data: {
-        message: 'No doc was found here!',
-      },
-    })
+    throw createDocsNotFoundError()
   }
 
   return fetchDocs({
@@ -49,11 +45,7 @@ export const loadDocsPage = async ({
   docsPath: string
 }) => {
   if (!branch || !docsRoot || !docsPath) {
-    throw notFound({
-      data: {
-        message: 'No doc was found here!',
-      },
-    })
+    throw createDocsNotFoundError()
   }
 
   return fetchDocsPage({