diff --git a/public/app/themes/clarity/inc/admin/plugins/wp-document-revisions.php b/public/app/themes/clarity/inc/admin/plugins/wp-document-revisions.php
index 3503ab41b..bfb6be294 100644
--- a/public/app/themes/clarity/inc/admin/plugins/wp-document-revisions.php
+++ b/public/app/themes/clarity/inc/admin/plugins/wp-document-revisions.php
@@ -20,6 +20,7 @@ class WPDocumentRevisions
 
     private $home_url = '';
     private $site_url = '';
+    private $wp_document_revisions = null;
 
     public function __construct()
     {
@@ -36,6 +37,8 @@ public function hooks(): void
         add_filter('document_permalink', [$this, 'filterPermalink'], 10, 2);
         // Filter using gzip, always return false, let nginx handle gzipping where necessary.
         add_filter('document_serve_use_gzip', '__return_false', null, 2);
+        // Filter to retry missing files.
+        add_filter('get_attached_file', [$this, 'retryFilesNotFound'], 15, 2);
     }
 
     /**
@@ -46,7 +49,6 @@ public function hooks(): void
      * 
      * @return string The filtered permalink.
      */
-
     public function filterPermalink(string $link, null|object|array $document)
     {
         // Do nothing if the document is published.
@@ -57,4 +59,88 @@ public function filterPermalink(string $link, null|object|array $document)
         // Remove unnecessary `/wp` from the link.
         return str_replace($this->site_url, $this->home_url, $link);
     }
+
+    /**
+     * Extract the date from the file path.
+     * 
+     * @param string $file The file path.
+     * @return string|null The date.
+     */
+    private function getDateFromFile(string $file): ?string
+    {
+        $matches = [];
+        preg_match('/\/media\/(\d{4}\/\d{2})\//', $file, $matches);
+        return $matches[1] ?? null;
+    }
+
+    /**
+     * Extract the date from the URL (guid).
+     * 
+     * @param string $url The URL.
+     * @return string|null The date.
+     */
+    private function getDateFromUrl(string $url): ?string
+    {
+        $matches = [];
+        preg_match('/\/documents\/(\d{4}\/\d{2})\//', $url, $matches);
+        return $matches[1] ?? null;
+    }
+
+    /**
+     * Retry missing document/file, with date from attachment guid.
+     * 
+     * This function has been added because files are not being served correctly 
+     * when the published date has been updated. In the function, we check if the 
+     * file exists, if it doesn't the we extract the date from the attachment's 
+     * guid and replace the date in the file path.
+     * 
+     * @param string $file The file path.
+     * @param int $attachment_id The attachment ID.
+     * @return string The file path.
+     */
+    public function retryFilesNotFound($file, $attachment_id)
+    {
+        if (!$file) {
+            return $file;
+        }
+
+        if (!$this->wp_document_revisions) {
+            // Make sure we are dealing with a document.
+            $this->wp_document_revisions = new \WP_Document_Revisions();
+        }
+
+        if (!$this->wp_document_revisions->verify_post_type($attachment_id)) {
+            return $file;
+        }
+
+        if (is_file($file)) {
+            return $file;
+        }
+
+        $attachment = get_post($attachment_id);
+
+        if (!$attachment) {
+            return $file;
+        }
+
+        $dates = [
+            'file' => $this->getDateFromFile($file),
+            'guid' => $this->getDateFromUrl($attachment->guid),
+        ];
+
+        if ($dates['file'] === $dates['guid'] || $dates['file'] === null || $dates['guid'] === null) {
+            return $file;
+        }
+
+        // Let's replace the date with the one from the attachment's guid.
+        $new_file = str_replace($dates['file'], $dates['guid'], $file);
+        
+        // If the new file exists, return it.
+        if (is_file($new_file)) {
+            return $new_file;
+        }
+
+        // If the file still doesn't exist, return the original file.
+        return $file;
+    }
 }