diff --git a/core/includes/install.core.inc b/core/includes/install.core.inc
index 7b66911..f8de4f1 100644
--- a/core/includes/install.core.inc
+++ b/core/includes/install.core.inc
@@ -2116,6 +2116,25 @@ function install_check_requirements($install_state) {
       }
     }
   }
+
+  // Installations on Windows can run into limitations with MAX_PATH if the
+  // Drupal root directory is too deep in the filesystem. Generally this shows
+  // up in cached Twig templates. Because of their variable length, for example
+  // template suggestions can arbitrarily lengthen a filename, there is no set
+  // limit beyond which Drupal will not function correctly on Windows. Thus we
+  // only warn if a Drupal is being installed more than 100 characters deep in
+  // the filesystem.
+  if (strpos(strtolower(php_uname('s')), 'win') === 0) {
+    $depth = strlen(realpath(DRUPAL_ROOT));
+    if ($depth > 100) {
+      $requirements['max_path_on_windows'] = [
+        'title' => t('Windows installation'),
+        'description' => t('The path length to the Drupal root directory (@depth characters) is greater than 100 characters. This may cause problems when running on a Windows server. It is recommended to install Drupal on Windows in a shorter path.', ['@depth' => $depth]),
+        'severity' => REQUIREMENT_WARNING,
+      ];
+    }
+  }
+
   return $requirements;
 }