diff --git a/core/modules/file/src/Plugin/Field/FieldWidget/FileWidget.php b/core/modules/file/src/Plugin/Field/FieldWidget/FileWidget.php
index fbc30d8..4dc6120 100644
--- a/core/modules/file/src/Plugin/Field/FieldWidget/FileWidget.php
+++ b/core/modules/file/src/Plugin/Field/FieldWidget/FileWidget.php
@@ -46,7 +46,7 @@ public function __construct($plugin_id, $plugin_definition, FieldDefinitionInter
    * {@inheritdoc}
    */
   public static function create(ContainerInterface $container, array $configuration, $plugin_id, $plugin_definition) {
-    return new static($plugin_id, $plugin_definition,$configuration['field_definition'], $configuration['settings'], $configuration['third_party_settings'], $container->get('element_info'));
+    return new static($plugin_id, $plugin_definition, $configuration['field_definition'], $configuration['settings'], $configuration['third_party_settings'], $container->get('element_info'));
   }
 
   /**
diff --git a/core/modules/image/src/Plugin/Field/FieldWidget/ImageWidget.php b/core/modules/image/src/Plugin/Field/FieldWidget/ImageWidget.php
index f202293..b2c50fa 100644
--- a/core/modules/image/src/Plugin/Field/FieldWidget/ImageWidget.php
+++ b/core/modules/image/src/Plugin/Field/FieldWidget/ImageWidget.php
@@ -7,11 +7,15 @@
 
 namespace Drupal\image\Plugin\Field\FieldWidget;
 
-use Drupal\Core\Field\FieldItemListInterface;
 use Drupal\Component\Utility\NestedArray;
+use Drupal\Core\Field\FieldDefinitionInterface;
+use Drupal\Core\Field\FieldItemListInterface;
 use Drupal\Core\Form\FormStateInterface;
+use Drupal\Core\Image\ImageFactory;
+use Drupal\Core\Render\ElementInfoManagerInterface;
 use Drupal\file\Entity\File;
 use Drupal\file\Plugin\Field\FieldWidget\FileWidget;
+use Symfony\Component\DependencyInjection\ContainerInterface;
 
 /**
  * Plugin implementation of the 'image_image' widget.
@@ -27,6 +31,36 @@
 class ImageWidget extends FileWidget {
 
   /**
+   * The image factory service.
+   *
+   * @var \Drupal\Core\Image\ImageFactory
+   */
+  protected $imageFactory;
+
+  /**
+   * {@inheritdoc}
+   */
+  public function __construct($plugin_id, $plugin_definition, FieldDefinitionInterface $field_definition, array $settings, array $third_party_settings, ElementInfoManagerInterface $element_info, ImageFactory $image_factory) {
+    parent::__construct($plugin_id, $plugin_definition, $field_definition, $settings, $third_party_settings, $element_info);
+    $this->imageFactory = $image_factory;
+  }
+
+  /**
+   * {@inheritdoc}
+   */
+  public static function create(ContainerInterface $container, array $configuration, $plugin_id, $plugin_definition) {
+    return new static(
+      $plugin_id,
+      $plugin_definition,
+      $configuration['field_definition'],
+      $configuration['settings'],
+      $configuration['third_party_settings'],
+      $container->get('element_info'),
+      $container->get('image.factory')
+    );
+  }
+
+  /**
    * {@inheritdoc}
    */
   public static function defaultSettings() {
@@ -121,11 +155,17 @@ public function formElement(FieldItemListInterface $items, $delta, array $elemen
       $element['#upload_validators']['file_validate_image_resolution'] = array($field_settings['max_resolution'], $field_settings['min_resolution']);
     }
 
-    // If not using custom extension validation, ensure this is an image.
-    $supported_extensions = array('png', 'gif', 'jpg', 'jpeg');
-    $extensions = isset($element['#upload_validators']['file_validate_extensions'][0]) ? $element['#upload_validators']['file_validate_extensions'][0] : implode(' ', $supported_extensions);
-    $extensions = array_intersect(explode(' ', $extensions), $supported_extensions);
-    $element['#upload_validators']['file_validate_extensions'][0] = implode(' ', $extensions);
+    // If using custom extension validation, ensure that the extensions are
+    // supported by the current image toolkit.
+    $supported_extensions = $this->imageFactory->getSupportedExtensions();
+    if (isset($element['#upload_validators']['file_validate_extensions'][0])) {
+      $extensions = $element['#upload_validators']['file_validate_extensions'][0];
+      $extensions = array_intersect(explode(' ', $extensions), $supported_extensions);
+      $element['#upload_validators']['file_validate_extensions'][0] = implode(' ', $extensions);
+    }
+    else {
+      $element['#upload_validators']['file_validate_extensions'][0] = implode(' ', $supported_extensions);
+    }
 
     // Add properties needed by process() method.
     $element['#preview_image_style'] = $this->getSetting('preview_image_style');
diff --git a/core/modules/system/src/Plugin/ImageToolkit/GDToolkit.php b/core/modules/system/src/Plugin/ImageToolkit/GDToolkit.php
index d16330f..2da5dea 100644
--- a/core/modules/system/src/Plugin/ImageToolkit/GDToolkit.php
+++ b/core/modules/system/src/Plugin/ImageToolkit/GDToolkit.php
@@ -347,7 +347,16 @@ public static function isAvailable() {
   public static function getSupportedExtensions() {
     $extensions = array();
     foreach (static::supportedTypes() as $image_type) {
-      $extensions[] = Unicode::strtolower(image_type_to_extension($image_type, FALSE));
+      $extension = Unicode::strtolower(image_type_to_extension($image_type, FALSE));
+      $extensions[] = $extension;
+      // Add some known similar extensions.
+      // @todo Figure out how to handle this better.
+      if ($extension === 'jpeg') {
+        $extensions[] = 'jpg';
+      }
+      elseif ($extension === 'tiff') {
+        $extensions[] = 'tif';
+      }
     }
     return $extensions;
   }