diff --git a/CHANGELOG.txt b/CHANGELOG.txt
index b1b2a9dc40..e8a387746d 100644
--- a/CHANGELOG.txt
+++ b/CHANGELOG.txt
@@ -4,6 +4,8 @@ Changelog
 1.6 (xx.xx.xxxx) - IN DEVELOPMENT
 ~~~~~~~~~~~~~~~~
 
+ * Image upload form in image chooser now performs client side validation so that the selected file is not lost in the submission (Jack Paine)
+
 
 1.5 (xx.xx.xxxx)
 ~~~~~~~~~~~~~~~~
diff --git a/docs/releases/1.6.rst b/docs/releases/1.6.rst
index b68f86626d..b3d02a5be2 100644
--- a/docs/releases/1.6.rst
+++ b/docs/releases/1.6.rst
@@ -14,6 +14,8 @@ What's new
 Minor features
 ~~~~~~~~~~~~~~
 
+ * Image upload form in image chooser now performs client side validation so that the selected file is not lost in the submission (Jack Paine)
+
 
 Bug fixes
 ~~~~~~~~~
diff --git a/wagtail/wagtailadmin/static_src/wagtailadmin/js/core.js b/wagtail/wagtailadmin/static_src/wagtailadmin/js/core.js
index 3d973e1aad..03d8ec56a4 100644
--- a/wagtail/wagtailadmin/static_src/wagtailadmin/js/core.js
+++ b/wagtail/wagtailadmin/static_src/wagtailadmin/js/core.js
@@ -221,15 +221,23 @@ $(function() {
         var $self = $(this);
         var $replacementElem = $('em', $self);
         var reEnableAfter = 30;
-        var dataName = 'disabledtimeout'
+        var dataName = 'disabledtimeout';
 
-        // Check the form this submit button belongs to (if any)
+        // Perform client-side validation on the form this submit button belongs to (if any)
         var form = $self.closest('form').get(0);
-        if (form && form.checkValidity && (form.checkValidity() == false)) {
-                 // ^ Check form.checkValidity returns something as it may not be browser compatible
+        if (form && form.checkValidity && (!form.checkValidity())) {
+            // form exists, browser provides a checkValidity method and checkValidity returns false
             return;
         }
 
+        window.cancelSpinner = function() {
+            $self.prop('disabled', '').removeData(dataName).removeClass('button-longrunning-active');
+
+            if ($self.data('clicked-text')) {
+                $replacementElem.text($self.data('original-text'));
+            }
+        };
+
         // Disabling a button prevents it submitting the form, so disabling
         // must occur on a brief timeout only after this function returns.
 
@@ -240,11 +248,7 @@ $(function() {
                 $self.data(dataName, setTimeout(function() {
                     clearTimeout($self.data(dataName));
 
-                    $self.prop('disabled', '').removeData(dataName).removeClass('button-longrunning-active')
-
-                    if ($self.data('clicked-text')) {
-                        $replacementElem.text($self.data('original-text'));
-                    }
+                    cancelSpinner();
 
                 }, reEnableAfter * 1000));
 
diff --git a/wagtail/wagtailimages/templates/wagtailimages/chooser/chooser.js b/wagtail/wagtailimages/templates/wagtailimages/chooser/chooser.js
index 30e07e1b5c..01e7bdb7aa 100644
--- a/wagtail/wagtailimages/templates/wagtailimages/chooser/chooser.js
+++ b/wagtail/wagtailimages/templates/wagtailimages/chooser/chooser.js
@@ -59,25 +59,26 @@ function(modal) {
     $('form.image-upload', modal.body).submit(function() {
         var formdata = new FormData(this);
 
-        $.ajax({
-            url: this.action,
-            data: formdata,
-            processData: false,
-            contentType: false,
-            type: 'POST',
-            dataType: 'text',
-            success: function(response){
-                modal.loadResponseText(response);
-            },
-            error: function(response, textStatus, errorThrown) {
-                {% trans "Server Error" as error_label %}
-                {% trans "Report this error to your webmaster with the following information:" as error_message %}
-                message = '{{ error_message|escapejs }}<br />' + errorThrown + ' - ' + response.status;
-                $('#upload').append(
-                    '<div class="help-block help-critical">' +
-                    '<strong>{{ error_label|escapejs }}: </strong>' + message + '</div>');
+        if ($('#id_title', modal.body).val() == '') {
+            var li = $('#id_title', modal.body).closest('li');
+            if (!li.hasClass('error')) {
+                li.addClass('error');
+                $('#id_title', modal.body).closest('.field-content').append('<p class="error-message"><span>This field is required.</span></p>')
             }
-        });
+            setTimeout(cancelSpinner, 500);
+        } else {
+            $.ajax({
+                url: this.action,
+                data: formdata,
+                processData: false,
+                contentType: false,
+                type: 'POST',
+                dataType: 'text',
+                success: function(response){
+                    modal.loadResponseText(response);
+                }
+            });
+        }
 
         return false;
     });