diff --git a/wagtail/wagtailimages/static/wagtailimages/js/add-multiple.js b/wagtail/wagtailimages/static/wagtailimages/js/add-multiple.js
index 962af60cd..f472c32aa 100644
--- a/wagtail/wagtailimages/static/wagtailimages/js/add-multiple.js
+++ b/wagtail/wagtailimages/static/wagtailimages/js/add-multiple.js
@@ -27,9 +27,22 @@ $(function(){
             var li = $($('#upload-list-item').html()).addClass('upload-uploading')
             var options = that.options;
 
+            console.log(data);
+
             $('#upload-list').append(li);
             data.context = li;
 
+            // check if initial File API validation failed.
+            if (data.files.error) {
+                console.log('here');
+                data.context.each(function (index) {
+                    var error = data.files[index].error;
+                    if (error) {
+                        $(this).find('.error_messages').text(error);
+                    }
+                });
+            }
+
             data.process(function () {
                 return $this.fileupload('process', data);
             }).always(function () {
@@ -46,14 +59,14 @@ $(function(){
                 if ((that._trigger('added', e, data) !== false) &&
                         (options.autoUpload || data.autoUpload) &&
                         data.autoUpload !== false) {
-                    data.submit();
+                    data.submit()
                 }
             }).fail(function () {
                 if (data.files.error) {
                     data.context.each(function (index) {
                         var error = data.files[index].error;
                         if (error) {
-                            $(this).find('.error').text(error);
+                            $(this).find('.error_messages').text(error);
                         }
                     });
                 }
diff --git a/wagtail/wagtailimages/templates/wagtailimages/multiple/add.html b/wagtail/wagtailimages/templates/wagtailimages/multiple/add.html
index 1859b68ce..fbf63563c 100644
--- a/wagtail/wagtailimages/templates/wagtailimages/multiple/add.html
+++ b/wagtail/wagtailimages/templates/wagtailimages/multiple/add.html
@@ -61,6 +61,7 @@
         <script src="{{ STATIC_URL }}wagtailimages/js/vendor/jquery.fileupload.js"></script>
         <script src="{{ STATIC_URL }}wagtailimages/js/vendor/jquery.fileupload-process.js"></script>
         <script src="{{ STATIC_URL }}wagtailimages/js/vendor/jquery.fileupload-image.js"></script>
+        <script src="{{ STATIC_URL }}wagtailimages/js/vendor/jquery.fileupload-validate.js"></script>
         <script src="{{ STATIC_URL }}wagtailadmin/js/vendor/tag-it.js"></script>
 
         <!-- Main script -->