diff --git a/src/utils/docs-redirects.ts b/src/utils/docs-redirects.ts
index 3565086ff..4ab83b43b 100644
--- a/src/utils/docs-redirects.ts
+++ b/src/utils/docs-redirects.ts
@@ -38,16 +38,19 @@ export function resolveDocsPathRedirect({
     return { type: 'not-found' }
   }
 
+  // Manifest paths already have one trailing /index removed. Preserve the
+  // requested path for loading so nested index/index files stay distinct.
+  const canonicalRequestedPath = canonicalizeDocsPath(requestedPath)
   const knownPaths = new Set(manifest.paths.map(normalizeManifestPath))
 
-  if (knownPaths.has(requestedPath)) {
+  if (knownPaths.has(canonicalRequestedPath)) {
     return { type: 'render', docsPath: requestedPath }
   }
 
   const redirectFromTarget = getRedirectTarget({
     knownPaths,
     manifest,
-    requestedPath,
+    requestedPath: canonicalRequestedPath,
   })
 
   if (redirectFromTarget !== null) {
@@ -58,7 +61,7 @@ export function resolveDocsPathRedirect({
     defaultDocs,
     frameworks,
     knownPaths,
-    requestedPath,
+    requestedPath: canonicalRequestedPath,
   })
 
   if (frameworkRedirectTarget !== null) {
@@ -67,7 +70,7 @@ export function resolveDocsPathRedirect({
 
   const sectionIndexRedirectTarget = getSectionIndexRedirectTarget({
     knownPaths,
-    requestedPath,
+    requestedPath: canonicalRequestedPath,
   })
 
   if (sectionIndexRedirectTarget !== null) {
@@ -87,8 +90,10 @@ export function docsManifestHasPath(
     return false
   }
 
+  const canonicalPath = canonicalizeDocsPath(normalizedPath)
+
   return manifest.paths.some(
-    (path) => normalizeManifestPath(path) === normalizedPath,
+    (path) => normalizeManifestPath(path) === canonicalPath,
   )
 }
 
@@ -220,10 +225,17 @@ function getSectionIndexRedirectTarget(opts: {
 }
 
 function normalizeManifestPath(path: string) {
-  return removeLeadingSlash(path.trim())
-    .replace(/\.md$/, '')
-    .replace(/\/index$/, '')
-    .replace(/\/+$/g, '')
+  const normalizedPath = removeLeadingSlash(path.trim()).replace(/\/+$/g, '')
+
+  if (normalizedPath.endsWith('.md')) {
+    return normalizedPath.replace(/\.md$/, '').replace(/\/index$/, '')
+  }
+
+  return normalizedPath
+}
+
+function canonicalizeDocsPath(path: string) {
+  return path.replace(/\/index$/, '')
 }
 
 function normalizeDocsPath(path: string | null | undefined) {
diff --git a/tests/docs-redirects.test.ts b/tests/docs-redirects.test.ts
index 77a907ca7..305687799 100644
--- a/tests/docs-redirects.test.ts
+++ b/tests/docs-redirects.test.ts
@@ -55,6 +55,23 @@ function assertRedirectsTo(opts: {
   )
 }
 
+function assertRenders(opts: {
+  defaultDocs: string
+  docsPath: string
+  frameworks: Array<string>
+  manifest: DocsRedirectManifest
+}) {
+  assert.deepEqual(
+    resolveDocsPathRedirect({
+      defaultDocs: opts.defaultDocs,
+      docsPath: opts.docsPath,
+      frameworks: opts.frameworks,
+      manifest: opts.manifest,
+    }),
+    { type: 'render', docsPath: opts.docsPath },
+  )
+}
+
 function assertNotFound(opts: {
   defaultDocs: string
   docsPath: string
@@ -160,6 +177,50 @@ assertNotFound({
   manifest: manifestWithPaths(['overview', 'framework/react/overview']),
 })
 
+const typedocManifest = manifestWithPaths([
+  'overview',
+  'reference',
+  'reference/index',
+  'reference/index/type-aliases/DebugOptions',
+  'framework/react/reference',
+  'framework/react/reference/index',
+])
+
+assertRenders({
+  defaultDocs: 'overview',
+  docsPath: 'reference/index',
+  frameworks: ['react'],
+  manifest: typedocManifest,
+})
+
+assertRenders({
+  defaultDocs: 'overview',
+  docsPath: 'reference/index/index',
+  frameworks: ['react'],
+  manifest: typedocManifest,
+})
+
+assertRenders({
+  defaultDocs: 'overview',
+  docsPath: 'reference/index/type-aliases/DebugOptions',
+  frameworks: ['react'],
+  manifest: typedocManifest,
+})
+
+assertRenders({
+  defaultDocs: 'overview',
+  docsPath: 'framework/react/reference/index',
+  frameworks: ['react'],
+  manifest: typedocManifest,
+})
+
+assertRenders({
+  defaultDocs: 'overview',
+  docsPath: 'framework/react/reference/index/index',
+  frameworks: ['react'],
+  manifest: typedocManifest,
+})
+
 assertRedirectsTo({
   defaultDocs: 'overview',
   docsPath: 'react/overview',
@@ -225,6 +286,14 @@ assert.equal(
   true,
 )
 
+assert.equal(
+  docsManifestHasPath(
+    manifestWithPaths(['reference/index']),
+    'reference/index/index',
+  ),
+  true,
+)
+
 assert.equal(
   docsManifestHasPath(
     manifestWithPaths(['guides/queries.md']),
diff --git a/tests/docs-route-smoke.test.ts b/tests/docs-route-smoke.test.ts
index 03807ab02..0f0806c21 100644
--- a/tests/docs-route-smoke.test.ts
+++ b/tests/docs-route-smoke.test.ts
@@ -56,6 +56,17 @@ test(
         })
       }
 
+      if (library.id === 'table') {
+        paths.push({
+          path: '/table/latest/docs/reference/index/index',
+          expected: 'ok',
+        })
+        paths.push({
+          path: '/table/latest/docs/framework/react/reference/index/index',
+          expected: 'ok',
+        })
+      }
+
       return paths
     })