diff --git a/core/lib/Drupal/Core/Asset/AssetResolver.php b/core/lib/Drupal/Core/Asset/AssetResolver.php
index 35d6608256..6945011b08 100644
--- a/core/lib/Drupal/Core/Asset/AssetResolver.php
+++ b/core/lib/Drupal/Core/Asset/AssetResolver.php
@@ -259,7 +259,7 @@ public function getJsAssets(AttachedAssetsInterface $assets, $optimize, Language
 
             // Always add a tiny value to the weight, to conserve the insertion
             // order.
-            $options['weight'] += count($javascript) / 1000;
+            $options['weight'] += count($javascript) / 30000;
 
             // Local and external files must keep their name as the associative
             // key so the same JavaScript file is not added twice.
diff --git a/core/modules/system/tests/modules/jqueryui_library_assets_test/jqueryui_library_assets_test.routing.yml b/core/modules/system/tests/modules/jqueryui_library_assets_test/jqueryui_library_assets_test.routing.yml
index cb2ad14524..5a8a815d1e 100644
--- a/core/modules/system/tests/modules/jqueryui_library_assets_test/jqueryui_library_assets_test.routing.yml
+++ b/core/modules/system/tests/modules/jqueryui_library_assets_test/jqueryui_library_assets_test.routing.yml
@@ -1,7 +1,15 @@
 jqueryui_library_asset_test_page:
-  path: '/jqueryui_library_assets_test/{library}'
+  path: '/jqueryui_library_assets_test'
   defaults:
     _controller: '\Drupal\jqueryui_library_assets_test\Controller\JqueryUiTestAssetsController::build'
     _title: 'Test jQuery UI asset loading order'
   requirements:
     _access: 'TRUE'
+
+jqueryui_library_asset_test_external:
+  path: '/jqueryui_library_assets_test_large'
+  defaults:
+    _controller: '\Drupal\jqueryui_library_assets_test\Controller\JqueryUiTestAssetsController::largeJavascriptDependencies'
+    _title: 'Test jQuery UI asset loading order with lots of intermediate assets'
+  requirements:
+    _access: 'TRUE'
diff --git a/core/modules/system/tests/modules/jqueryui_library_assets_test/src/Controller/JqueryUiTestAssetsController.php b/core/modules/system/tests/modules/jqueryui_library_assets_test/src/Controller/JqueryUiTestAssetsController.php
index 2db6550c68..4befade8f8 100644
--- a/core/modules/system/tests/modules/jqueryui_library_assets_test/src/Controller/JqueryUiTestAssetsController.php
+++ b/core/modules/system/tests/modules/jqueryui_library_assets_test/src/Controller/JqueryUiTestAssetsController.php
@@ -3,6 +3,7 @@
 namespace Drupal\jqueryui_library_assets_test\Controller;
 
 use Drupal\Core\Controller\ControllerBase;
+use Symfony\Component\HttpFoundation\Request;
 
 /**
  * Controller for testing jQuery UI asset loading order.
@@ -12,23 +13,31 @@ class JqueryUiTestAssetsController extends ControllerBase {
   /**
    * Provides a page that loads a library.
    *
-   * @param string $library
-   *   A pipe delimited list of library names.
+   * @param \Symfony\Component\HttpFoundation\Request $request
+   *   The current request object, typically containing "library" query
+   *   containing a pipe delimited list of library names.
    *
    * @return array
    *   The render array.
    */
-  public function build($library) {
+  public function build(Request $request) {
+    // @see https://www.drupal.org/project/drupal/issues/2741939
+    $library = $request->query->get('library', '');
     // If there are pipes in $library, they are separating multiple library
     // names.
     if (strpos($library, '|') !== FALSE) {
       $library = explode('|', $library);
       $library = array_map(function ($item) {
-        return "core/$item";
+        if (strpos($item, '/') === FALSE) {
+          return "core/$item";
+        }
+        return $item;
       }, $library);
     }
     else {
-      $library = "core/$library";
+      if (strpos($library, '/') === FALSE) {
+        $library = "core/$library";
+      }
     }
 
     return [
@@ -36,6 +45,35 @@ public function build($library) {
       '#attached' => [
         'library' => $library,
       ],
+      '#cache' => [
+        'max-age' => 0,
+        'contexts' => [
+          'url.path',
+          'url.query_args:library',
+        ],
+      ],
+    ];
+  }
+
+  /**
+   * Provides a page that loads jQuery UI as a library.
+   *
+   * With a large third party library in the middle of two other jquery.ui
+   * dependents.
+   *
+   * @return array
+   *   The render array.
+   */
+  public function largeJavascriptDependencies() {
+    return [
+      '#markup' => 'I am a page for testing jQuery UI asset loading order when large asset dependencies are involved between two jquery.ui dependents.',
+      '#attached' => [
+        'library' => [
+          'core/drupal.dialog',
+          'jqueryui_library_assets_test/many-dependencies',
+          'core/drupal.autocomplete',
+        ],
+      ],
     ];
   }
 
diff --git a/core/tests/Drupal/FunctionalTests/Libraries/JqueryUiLibraryAssetsTest.php b/core/tests/Drupal/FunctionalTests/Libraries/JqueryUiLibraryAssetsTest.php
index f92fd3c535..02d42f4fcc 100644
--- a/core/tests/Drupal/FunctionalTests/Libraries/JqueryUiLibraryAssetsTest.php
+++ b/core/tests/Drupal/FunctionalTests/Libraries/JqueryUiLibraryAssetsTest.php
@@ -216,7 +216,7 @@ protected function trimFilePath($path) {
    * @dataProvider providerTestAssetLoading
    */
   public function testLibraryAssetLoadingOrder($library) {
-    $this->drupalGet("jqueryui_library_assets_test/$library");
+    $this->drupalGet('jqueryui_library_assets_test', ['query' => ['library' => $library]]);
     $this->assertSession()->statusCodeEquals(200);
 
     // A pipe character in $libraries is delimiting multiple library names.
@@ -227,6 +227,10 @@ public function testLibraryAssetLoadingOrder($library) {
     // libraries being tested. This will be used to confirm the configured
     // assets actually load on the test page.
     foreach ($libraries as $library_name) {
+      if (strpos($library_name, '/') !== FALSE) {
+        // Ignore if it's an external library.
+        continue;
+      }
       foreach (['css', 'js'] as $type) {
         $assets = $this->coreLibrariesWithJqueryUiAssets[$library_name][$type];
         foreach ($assets as $asset) {
@@ -297,7 +301,7 @@ public function testLibraryAssetLoadingOrder($library) {
    * @dataProvider providerTestAssetLoading
    */
   public function testAssetLoadingUnchanged($library, array $expected_css, array $expected_js) {
-    $this->drupalGet("jqueryui_library_assets_test/$library");
+    $this->drupalGet('jqueryui_library_assets_test', ['query' => ['library' => $library]]);
     $this->assertSession()->statusCodeEquals(200);
 
     // Find all jQuery UI CSS files loaded to the page.
@@ -345,6 +349,90 @@ public function testAssetLoadingUnchanged($library, array $expected_css, array $
    */
   public function providerTestAssetLoading() {
     return [
+      'drupal.dialog|drupal.autocomplete' => [
+        'library' => 'drupal.dialog|drupal.autocomplete',
+        'expected_css' => [
+          'core/assets/vendor/jquery.ui/themes/base/core.css',
+          'core/assets/vendor/jquery.ui/themes/base/controlgroup.css',
+          'core/assets/vendor/jquery.ui/themes/base/autocomplete.css',
+          'core/assets/vendor/jquery.ui/themes/base/menu.css',
+          'core/assets/vendor/jquery.ui/themes/base/checkboxradio.css',
+          'core/assets/vendor/jquery.ui/themes/base/resizable.css',
+          'core/assets/vendor/jquery.ui/themes/base/button.css',
+          'core/assets/vendor/jquery.ui/themes/base/dialog.css',
+          'core/assets/vendor/jquery.ui/themes/base/theme.css',
+        ],
+        'expected_js' => [
+          'core/assets/vendor/jquery.ui/ui/data-min.js',
+          'core/assets/vendor/jquery.ui/ui/disable-selection-min.js',
+          'core/assets/vendor/jquery.ui/ui/escape-selector-min.js',
+          'core/assets/vendor/jquery.ui/ui/focusable-min.js',
+          'core/assets/vendor/jquery.ui/ui/form-min.js',
+          'core/assets/vendor/jquery.ui/ui/form-reset-mixin-min.js',
+          'core/assets/vendor/jquery.ui/ui/ie-min.js',
+          'core/assets/vendor/jquery.ui/ui/jquery-1-7-min.js',
+          'core/assets/vendor/jquery.ui/ui/keycode-min.js',
+          'core/assets/vendor/jquery.ui/ui/labels-min.js',
+          'core/assets/vendor/jquery.ui/ui/plugin-min.js',
+          'core/assets/vendor/jquery.ui/ui/safe-active-element-min.js',
+          'core/assets/vendor/jquery.ui/ui/safe-blur-min.js',
+          'core/assets/vendor/jquery.ui/ui/scroll-parent-min.js',
+          'core/assets/vendor/jquery.ui/ui/unique-id-min.js',
+          'core/assets/vendor/jquery.ui/ui/version-min.js',
+          'core/assets/vendor/jquery.ui/ui/widget-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/autocomplete-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/button-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/checkboxradio-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/controlgroup-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/dialog-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/draggable-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/menu-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/mouse-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/resizable-min.js',
+        ],
+      ],
+      'drupal.dialog|jqueryui_library_assets_test/many-dependencies|drupal.autocomplete' => [
+        'library' => 'drupal.dialog|jqueryui_library_assets_test/many-dependencies|drupal.autocomplete',
+        'expected_css' => [
+          'core/assets/vendor/jquery.ui/themes/base/core.css',
+          'core/assets/vendor/jquery.ui/themes/base/controlgroup.css',
+          'core/assets/vendor/jquery.ui/themes/base/autocomplete.css',
+          'core/assets/vendor/jquery.ui/themes/base/menu.css',
+          'core/assets/vendor/jquery.ui/themes/base/checkboxradio.css',
+          'core/assets/vendor/jquery.ui/themes/base/resizable.css',
+          'core/assets/vendor/jquery.ui/themes/base/button.css',
+          'core/assets/vendor/jquery.ui/themes/base/dialog.css',
+          'core/assets/vendor/jquery.ui/themes/base/theme.css',
+        ],
+        'expected_js' => [
+          'core/assets/vendor/jquery.ui/ui/data-min.js',
+          'core/assets/vendor/jquery.ui/ui/disable-selection-min.js',
+          'core/assets/vendor/jquery.ui/ui/escape-selector-min.js',
+          'core/assets/vendor/jquery.ui/ui/focusable-min.js',
+          'core/assets/vendor/jquery.ui/ui/form-min.js',
+          'core/assets/vendor/jquery.ui/ui/form-reset-mixin-min.js',
+          'core/assets/vendor/jquery.ui/ui/ie-min.js',
+          'core/assets/vendor/jquery.ui/ui/jquery-1-7-min.js',
+          'core/assets/vendor/jquery.ui/ui/keycode-min.js',
+          'core/assets/vendor/jquery.ui/ui/labels-min.js',
+          'core/assets/vendor/jquery.ui/ui/plugin-min.js',
+          'core/assets/vendor/jquery.ui/ui/safe-active-element-min.js',
+          'core/assets/vendor/jquery.ui/ui/safe-blur-min.js',
+          'core/assets/vendor/jquery.ui/ui/scroll-parent-min.js',
+          'core/assets/vendor/jquery.ui/ui/unique-id-min.js',
+          'core/assets/vendor/jquery.ui/ui/version-min.js',
+          'core/assets/vendor/jquery.ui/ui/widget-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/autocomplete-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/button-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/checkboxradio-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/controlgroup-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/dialog-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/draggable-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/menu-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/mouse-min.js',
+          'core/assets/vendor/jquery.ui/ui/widgets/resizable-min.js',
+        ],
+      ],
       'drupal.autocomplete' => [
         'library' => 'drupal.autocomplete',
         'expected_css' => [