diff --git a/forms/HtmlEditorField.php b/forms/HtmlEditorField.php
index ead1d5ff0..8cfabd8d4 100644
--- a/forms/HtmlEditorField.php
+++ b/forms/HtmlEditorField.php
@@ -422,14 +422,19 @@ class HtmlEditorField_Toolbar extends RequestHandler {
 		$fields = new FieldList(
 			new LiteralField(
 				'Heading',
-				sprintf('<h3>%s</h3>', _t('HtmlEditorField.IMAGE', 'Insert Image'))
+				sprintf('<h3 class="htmleditorfield-mediaform-heading insert">%s</h3>', _t('HtmlEditorField.INSERTIMAGE', 'Insert Image')).
+				sprintf('<h3 class="htmleditorfield-mediaform-heading update">%s</h3>', _t('HtmlEditorField.UpdateIMAGE', 'Update Image'))
 			),
 			$allFields
 		);
 		
 		$actions = new FieldList(
 			FormAction::create('insertimage', _t('HtmlEditorField.BUTTONINSERT', 'Insert'))
-				->addExtraClass('ss-ui-action-constructive')
+				->addExtraClass('ss-ui-action-constructive image-insert')
+				->setAttribute('data-icon', 'accept')
+				->setUseButtonTag(true),
+			FormAction::create('insertimage', _t('HtmlEditorField.BUTTONUpdate', 'Update'))
+				->addExtraClass('ss-ui-action-constructive image-update')
 				->setAttribute('data-icon', 'accept')
 				->setUseButtonTag(true)
 		);
diff --git a/javascript/HtmlEditorField.js b/javascript/HtmlEditorField.js
index a2a3af7e9..944924473 100644
--- a/javascript/HtmlEditorField.js
+++ b/javascript/HtmlEditorField.js
@@ -653,6 +653,21 @@ ss.editorWrappers['default'] = ss.editorWrappers.tinyMCE;
 		 * of remove files as well.
 		 */
 		$('form.htmleditorfield-mediaform').entwine({
+			onmatch: function() {
+				this.toggleLooks();
+				this._super();
+			},
+			toggleLooks: function(){
+				var updateExisting = Boolean(this.find('.ss-htmleditorfield-file').length);
+				this.find('.htmleditorfield-mediaform-heading.insert')[updateExisting ? 'hide' : 'show']();
+				this.find('.Actions .image-insert')[updateExisting ? 'hide' : 'show']();
+				this.find('.htmleditorfield-mediaform-heading.update')[updateExisting ? 'show' : 'hide']();
+				this.find('.Actions .image-update')[updateExisting ? 'show' : 'hide']();
+			},
+			toggleCloseButton: function(){
+				var updateExisting = Boolean(this.find('.ss-htmleditorfield-file').length);
+				this.find('.overview .action-delete')[updateExisting ? 'hide' : 'show']();
+			},
 			onsubmit: function() {
 				var self = this, ed = this.getEditor();
 
@@ -674,15 +689,15 @@ ss.editorWrappers['default'] = ss.editorWrappers.tinyMCE;
 				if(node.is('img')) {
 					this.showFileView(node.attr('src'), function() {
 						$(this).updateFromNode(node);
+						self.toggleCloseButton();
 						self.redraw();
 					});
 				}
-
+				this.toggleLooks();
 				this.redraw();
 			},
 			redraw: function() {
 				this._super();
-
 				var ed = this.getEditor(), node = $(ed.getSelectedNode()),
 					hasItems = Boolean(this.find('.ss-htmleditorfield-file').length),
 					editingSelected = node.is('img');