diff --git a/RELEASE_NOTES.md b/RELEASE_NOTES.md
index 1883d530bf2..8f5df265e4e 100644
--- a/RELEASE_NOTES.md
+++ b/RELEASE_NOTES.md
@@ -18,6 +18,7 @@ This serves two purposes:
 ### Changed
 - Realtime Compiler: The `DashboardController` class is now marked as internal, as it is not intended to be used outside of the package https://github.com/hydephp/develop/pull/1394
 - Updated the realtime compiler server configuration options in https://github.com/hydephp/develop/pull/1395 (backwards compatible)
+- Updated the realtime compiler to generate the documentation search index each time it's requested in https://github.com/hydephp/develop/pull/1405 (fixes https://github.com/hydephp/develop/issues/1404)
 
 ### Deprecated
 - for soon-to-be removed features.
@@ -31,6 +32,7 @@ This serves two purposes:
 - Updated the vendor publish command to support parent Laravel Prompts implementation in https://github.com/hydephp/develop/pull/1388
 - Fixed wrong version constant in https://github.com/hydephp/develop/pull/1391
 - Fixed improperly formatted exception message in https://github.com/hydephp/develop/pull/1399
+- Fixed missing support for missing and out of date search indexes when previewing site https://github.com/hydephp/develop/issues/1404 in https://github.com/hydephp/develop/pull/1405
 
 ### Security
 - in case of vulnerabilities.
diff --git a/docs/creating-content/documentation-pages.md b/docs/creating-content/documentation-pages.md
index 752498e7ce5..c3694d3350f 100644
--- a/docs/creating-content/documentation-pages.md
+++ b/docs/creating-content/documentation-pages.md
@@ -292,12 +292,9 @@ navigation menu items are hidden. The page will still be accessible as normal bu
 ]
 ```
 
-### Search with realtime compiler
-
-While the Realtime Compiler (what powers the `php hyde serve` command) serves the search index, however, it does not
-compile the index automatically. So if you're missing the search when previewing your site, run either `php hyde build`
-or `php hyde build:search` to compile the search index.
+### Live search with the realtime compiler
 
+The Realtime Compiler that powers the `php hyde serve` command will automatically generate a fresh search index each time the browser requests it.
 
 ## Automatic "Edit Page" button
 
diff --git a/packages/realtime-compiler/src/Routing/Router.php b/packages/realtime-compiler/src/Routing/Router.php
index 49aa7169d15..9b3ca859784 100644
--- a/packages/realtime-compiler/src/Routing/Router.php
+++ b/packages/realtime-compiler/src/Routing/Router.php
@@ -8,10 +8,13 @@
 use Hyde\RealtimeCompiler\Actions\AssetFileLocator;
 use Hyde\RealtimeCompiler\Concerns\SendsErrorResponses;
 use Hyde\RealtimeCompiler\Models\FileObject;
+use Hyde\RealtimeCompiler\Concerns\InteractsWithLaravel;
+use Hyde\Framework\Actions\GeneratesDocumentationSearchIndex;
 
 class Router
 {
     use SendsErrorResponses;
+    use InteractsWithLaravel;
 
     protected Request $request;
 
@@ -71,6 +74,10 @@ protected function shouldProxy(Request $request): bool
      */
     protected function proxyStatic(): Response
     {
+        if ($this->request->path === '/docs/search.json') {
+            $this->generateSearchIndex();
+        }
+
         $path = AssetFileLocator::find($this->request->path);
 
         if ($path === null) {
@@ -86,4 +93,14 @@ protected function proxyStatic(): Response
             'Content-Length' => $file->getContentLength(),
         ]);
     }
+
+    /**
+     * Generate the documentation search index.
+     */
+    protected function generateSearchIndex(): void
+    {
+        $this->bootApplication();
+
+        GeneratesDocumentationSearchIndex::handle();
+    }
 }