diff --git a/app/Http/Controllers/ShowDocumentationController.php b/app/Http/Controllers/ShowDocumentationController.php
index 5936f4a8f..50a0c5482 100644
--- a/app/Http/Controllers/ShowDocumentationController.php
+++ b/app/Http/Controllers/ShowDocumentationController.php
@@ -30,7 +30,9 @@ public function __invoke(Request $request, string $platform, string $version, ?s
         session(['viewing_docs_version' => $version]);
         session(['viewing_docs_platform' => $platform]);
 
-        $navigation = $this->cacheOrCompute("docs_nav_{$platform}_{$version}",
+        $fingerprint = $this->fingerprint($platform, $version);
+
+        $navigation = $this->cacheOrCompute("docs_nav_{$platform}_{$version}", $fingerprint,
             fn () => $this->getNavigation($platform, $version)
         );
 
@@ -39,7 +41,7 @@ public function __invoke(Request $request, string $platform, string $version, ?s
         }
 
         try {
-            $pageProperties = $this->cacheOrCompute("docs_{$platform}_{$version}_{$page}",
+            $pageProperties = $this->cacheOrCompute("docs_{$platform}_{$version}_{$page}", $fingerprint,
                 fn () => $this->getPageProperties($platform, $version, $page)
             );
         } catch (InvalidArgumentException $e) {
@@ -85,18 +87,50 @@ public function __invoke(Request $request, string $platform, string $version, ?s
      * docs edits show up immediately without clearing (or racing on) the cache.
      * The key folds in `config('docs')` so a Jump version bump invalidates
      * rendered pages instead of trailing by up to a day.
+     *
+     * The entry also carries a fingerprint of the markdown it was built from
+     * and is rebuilt as soon as that stops matching. Deploys ship new docs
+     * without clearing the application cache, so the TTL alone leaves an
+     * edited page — and the sidebar rendered alongside it — up to a day behind
+     * the files. Entries written before the fingerprint existed have none, so
+     * they miss and rebuild on the first request.
      */
-    private function cacheOrCompute(string $key, Closure $callback): mixed
+    private function cacheOrCompute(string $key, string $fingerprint, Closure $callback): mixed
     {
         if (config('app.env') === 'local') {
             return $callback();
         }
 
-        return Cache::remember(
-            $key.'_'.substr(md5(serialize(config('docs'))), 0, 8),
-            now()->addDay(),
-            $callback
-        );
+        $key = $key.'_'.substr(md5(serialize(config('docs'))), 0, 8);
+
+        $cached = Cache::get($key);
+
+        if (Arr::get($cached, 'fingerprint') === $fingerprint) {
+            return $cached['value'];
+        }
+
+        $value = $callback();
+
+        Cache::put($key, ['fingerprint' => $fingerprint, 'value' => $value], now()->addDay());
+
+        return $value;
+    }
+
+    /**
+     * A signature of every markdown file behind a platform's version — names
+     * and modification times, without reading any content.
+     */
+    private function fingerprint(string $platform, string $version): string
+    {
+        $files = (new Finder)
+            ->files()
+            ->name('*.md')
+            ->in(resource_path("views/docs/{$platform}/{$version}"));
+
+        return md5(collect($files)
+            ->map(fn (SplFileInfo $file): string => $file->getRelativePathname().'@'.$file->getMTime())
+            ->sort()
+            ->implode('|'));
     }
 
     public function serveRawMarkdown(Request $request, string $platform, string $version, string $page)
diff --git a/tests/Feature/Docs/DocsCachingTest.php b/tests/Feature/Docs/DocsCachingTest.php
index 5ab784f2e..2c08e658d 100644
--- a/tests/Feature/Docs/DocsCachingTest.php
+++ b/tests/Feature/Docs/DocsCachingTest.php
@@ -60,4 +60,85 @@ public function test_non_local_docs_request_caches_page_properties(): void
 
         $this->assertTrue(Cache::has($key));
     }
+
+    public function test_page_cache_is_reused_while_the_markdown_is_unchanged(): void
+    {
+        config(['app.env' => 'production']);
+
+        $this->get('/docs/mobile/4/edge-components/stack')->assertStatus(200);
+
+        $entry = Cache::get($this->pageCacheKey());
+        $entry['value']['content'] = '<p>Served from the cache</p>';
+        Cache::put($this->pageCacheKey(), $entry, now()->addDay());
+
+        $this->get('/docs/mobile/4/edge-components/stack')
+            ->assertStatus(200)
+            ->assertSee('Served from the cache', false);
+    }
+
+    public function test_page_cache_is_rebuilt_once_the_markdown_changes(): void
+    {
+        config(['app.env' => 'production']);
+
+        Cache::put($this->pageCacheKey(), [
+            'fingerprint' => 'built-from-older-markdown',
+            'value' => $this->stalePageProperties(),
+        ], now()->addDay());
+
+        $this->get('/docs/mobile/4/edge-components/stack')
+            ->assertStatus(200)
+            ->assertDontSee('Stale content');
+    }
+
+    public function test_page_cached_before_fingerprinting_is_rebuilt(): void
+    {
+        config(['app.env' => 'production']);
+
+        Cache::put($this->pageCacheKey(), $this->stalePageProperties(), now()->addDay());
+
+        $this->get('/docs/mobile/4/edge-components/stack')
+            ->assertStatus(200)
+            ->assertDontSee('Stale content');
+    }
+
+    public function test_navigation_cached_before_fingerprinting_is_rebuilt(): void
+    {
+        config(['app.env' => 'production']);
+
+        $key = 'docs_nav_mobile_4_'.substr(md5(serialize(config('docs'))), 0, 8);
+        Cache::put($key, [['path' => '/docs/mobile/4/removed-page', 'title' => 'Removed', 'order' => 0]], now()->addDay());
+
+        $response = $this->get('/docs/mobile/4');
+
+        $response->assertStatus(301);
+        $this->assertStringNotContainsString('removed-page', (string) $response->headers->get('Location'));
+    }
+
+    private function pageCacheKey(): string
+    {
+        return 'docs_mobile_4_edge-components/stack_'.substr(md5(serialize(config('docs'))), 0, 8);
+    }
+
+    /**
+     * Page properties in the shape the view expects, so a cache entry that is
+     * wrongly trusted renders rather than erroring — the assertion, not an
+     * exception, is what reports the failure.
+     *
+     * @return array<string, mixed>
+     */
+    private function stalePageProperties(): array
+    {
+        return [
+            'platform' => 'mobile',
+            'version' => '4',
+            'pagePath' => 'docs/mobile/4/edge-components/stack',
+            'title' => 'Stale',
+            'content' => '<p>Stale content</p>',
+            'tableOfContents' => [],
+            'navigation' => '',
+            'editUrl' => '',
+            'nextPage' => null,
+            'previousPage' => null,
+        ];
+    }
 }