diff --git a/core/modules/file/src/Element/ManagedFile.php b/core/modules/file/src/Element/ManagedFile.php
index 8e7843fcbb..06bf2e62a1 100644
--- a/core/modules/file/src/Element/ManagedFile.php
+++ b/core/modules/file/src/Element/ManagedFile.php
@@ -85,6 +85,7 @@ public static function valueCallback(&$element, $input, FormStateInterface $form
         // does for #element_validate and #process, this fills the missing
         // functionality to allow File fields to be extended through FAPI.
         if (isset($element['#file_value_callbacks'])) {
+          \Drupal::logger('file')->notice('#file_value_callbacks: '. serialize($element['#file_value_callbacks']));
           foreach ($element['#file_value_callbacks'] as $callback) {
             $callback($element, $input, $form_state);
           }
@@ -123,23 +124,32 @@ public static function valueCallback(&$element, $input, FormStateInterface $form
             $fids = [];
           }
         }
+        else {
+          \Drupal::logger('file')->notice('$input[\'fids\'] empty at line 95 in ManagedFile::valueCallback()');
+        }
       }
     }
+    else {
+      \Drupal::logger('file')->notice('Input is FALSE in ManagedFile::valueCallback()');
+    }
 
     // If there is no input or if the default value was requested above, use the
     // default value.
     if ($input === FALSE || $force_default) {
       if ($element['#extended']) {
+        \Drupal::logger('file')->notice('$element[\'#extended\']');
         $default_fids = isset($element['#default_value']['fids']) ? $element['#default_value']['fids'] : [];
         $return = isset($element['#default_value']) ? $element['#default_value'] : ['fids' => []];
       }
       else {
+        \Drupal::logger('file')->notice('$element[\'#extended\'] FALSE');
         $default_fids = isset($element['#default_value']) ? $element['#default_value'] : [];
         $return = ['fids' => []];
       }
 
       // Confirm that the file exists when used as a default value.
       if (!empty($default_fids)) {
+        \Drupal::logger('file')->notice('empty $default_fids');
         $fids = [];
         foreach ($default_fids as $fid) {
           if ($file = File::load($fid)) {
@@ -149,6 +159,11 @@ public static function valueCallback(&$element, $input, FormStateInterface $form
       }
     }
 
+    if (empty($fids)) {
+      $fids = [];
+      \Drupal::logger('file')->notice('fids empty, line 164 in ManagedFile');
+    }
+
     $return['fids'] = $fids;
     return $return;
   }
diff --git a/core/modules/media_library/src/Form/FileUploadForm.php b/core/modules/media_library/src/Form/FileUploadForm.php
index 81367821c2..2cb3e9d5be 100644
--- a/core/modules/media_library/src/Form/FileUploadForm.php
+++ b/core/modules/media_library/src/Form/FileUploadForm.php
@@ -253,6 +253,7 @@ public function processUploadElement(array $element, FormStateInterface $form_st
    *   The form state.
    */
   public function uploadButtonSubmit(array $form, FormStateInterface $form_state) {
+    \Drupal::logger('file')->notice('FileUploadForm::uploadButtonSubmit upload values:' . serialize($form_state->getValue('upload', [])));
     $files = $this->entityTypeManager
       ->getStorage('file')
       ->loadMultiple($form_state->getValue('upload', []));
diff --git a/core/modules/media_library/tests/src/FunctionalJavascript/UploadFail.php b/core/modules/media_library/tests/src/FunctionalJavascript/UploadFail.php
index 6992a03624..a1a8a0c56e 100644
--- a/core/modules/media_library/tests/src/FunctionalJavascript/UploadFail.php
+++ b/core/modules/media_library/tests/src/FunctionalJavascript/UploadFail.php
@@ -4,9 +4,11 @@
 
 use Behat\Mink\Exception\ElementNotFoundException;
 use Drupal\Core\File\Exception\FileNotExistsException;
+use Drupal\Core\File\FileSystemInterface;
 use Drupal\FunctionalJavascriptTests\WebDriverTestBase;
 use Drupal\media\Entity\Media;
 use Drupal\Tests\TestFileCreationTrait;
+use PHPUnit\Framework\AssertionFailedError;
 
 /**
  * Checks if uploads fail after several attempts.
@@ -23,6 +25,7 @@ class UploadFail extends WebDriverTestBase {
   protected static $modules = [
     'media_library_test',
     'node',
+    'dblog',
   ];
 
   /**
@@ -58,18 +61,41 @@ public function testManyConsecutiveUploads() {
     // Visit a node create page and open the media library.
     $this->drupalGet('node/add/basic_page');
 
+    $database = $this->container->get('database');
+
     $count = 0;
     // Upload then remove an image 100x to see if/when it fails.
     while ($count < 100) {
+      \Drupal::logger('file')->notice("Starting iteration $count");
       $this->assertElementExistsAfterWait('css', '.media-library-open-button[name^="field_twin_media"]', 10000, "Twin media open button not found on iteration $count")->click();
       $this->assertElementExistsAfterWait('css', '.media-library-menu', 10000, "Media library menu did not appear on iteration $count");
       $this->waitForText('Add or select media', 10000, "Text 'Add or select media' not appear on iteration $count");
       $this->clickTypeTab('Four');
-      $new_filename = uniqid() . '.jpg';
+      $new_filename = uniqid(time()) . '.jpg';
       $new_filepath = $file_system->realpath('public://') . '/' . $new_filename;
-      copy($file_system->realpath($jpg_image->uri), $new_filepath);
+      $file_system->copy($file_system->realpath($jpg_image->uri), $new_filepath);
       $this->waitForFieldExists('Add files', 10000, "Did not find 'Add files' on iteration $count");
+      $media_count = $database->select('file_managed')->countQuery()->execute()->fetchField();
+      $this->assertEquals($count, $media_count);
       $page->attachFileToField('Add files', $new_filepath);
+      $result = $page->waitFor(10, function () use ($database, $count) {
+        $media_count = $database->select('file_managed')->countQuery()->execute()->fetchField();
+        return ($count + 1) === intval($media_count);
+      });
+      if (!$result) {
+        $logs = $database
+          ->select('watchdog', 'w')
+          ->fields('w', ['message', 'variables'])
+          ->condition('type', 'file')
+          ->orderBy('wid', 'ASC')
+          ->execute()
+          ->fetchAll();
+        $output = "The file_managed table not updated on iteration $count.";
+        foreach ($logs as $log) {
+          $output .= "\n" . $log->message;
+        }
+        throw new AssertionFailedError($output);
+      }
       $this->waitForText('Alternative text', 10000, "Alternative text field not found on iteration $count");
       $field = $page->findField('Alternative text');
       $this->assertTrue(!empty($field), "Alt text label found but not the field on iteration $count");
@@ -86,6 +112,7 @@ public function testManyConsecutiveUploads() {
       $this->assertElementExistsAfterWait('css', '[name="field_twin_media-0-media-library-remove-button"]', 10000, "Media remove button not found on iteration $count")->click();
       $this->waitForText('2 media items remaining', 10000, "'2 media items remaining' not found on iteration $count");
       $count++;
+      $this->resetAll();
       usleep(10000);
     }
 
@@ -211,8 +238,6 @@ protected function waitForFieldExists($field, $timeout = 10000, $message = 'did
     } while (microtime(TRUE) < $end);
 
     $this->htmlOutput();
-    $filename = $this->htmlOutputDirectory . '/' . $this->htmlOutputClassName . '-' . $this->htmlOutputCounter . '-' . $this->htmlOutputTestId . '-waitFieExis.jpg';    $this->createScreenshot($filename);
-
     $this->assertNotEmpty($node, $message);
   }