diff --git src/wp-includes/js/tinymce/plugins/wpview/plugin.js src/wp-includes/js/tinymce/plugins/wpview/plugin.js
index 75f7047..337b3d2 100644
--- src/wp-includes/js/tinymce/plugins/wpview/plugin.js
+++ src/wp-includes/js/tinymce/plugins/wpview/plugin.js
@@ -265,12 +265,20 @@ tinymce.PluginManager.add( 'wpview', function( editor ) {
 		});
 
 		editor.dom.bind( editor.getBody(), 'mousedown mouseup click', function( event ) {
-			var view = getParentView( event.target );
+			var view = getParentView( event.target ),
+				deselectEventType;
 
 			// Contain clicks inside the view wrapper
 			if ( view ) {
 				event.stopPropagation();
 
+				// Hack to try and keep the block resize handles from appearing. They will show on mousedown and then be removed on mouseup.
+				if ( tinymce.Env.ie <= 10 ) {
+					deselect();
+				}
+
+				select( view );
+
 				if ( event.type === 'click' && ! event.metaKey && ! event.ctrlKey ) {
 					if ( editor.dom.hasClass( event.target, 'edit' ) ) {
 						wp.mce.views.edit( view );
@@ -278,12 +286,20 @@ tinymce.PluginManager.add( 'wpview', function( editor ) {
 						editor.dom.remove( view );
 					}
 				}
-				select( view );
 				// Returning false stops the ugly bars from appearing in IE11 and stops the view being selected as a range in FF.
 				// Unfortunately, it also inhibits the dragging of views to a new location.
 				return false;
 			} else {
-				if ( event.type === 'mousedown' ) {
+
+				// Fix issue with deselecting a view in IE8. Without this hack, clicking content above the view wouldn't actually deselect it
+				// and the caret wouldn't be placed at the mouse location
+				if( tinymce.Env.ie <= 8 ) {
+					deselectEventType = 'mouseup';
+				} else {
+					deselectEventType = 'mousedown';
+				}
+
+				if ( event.type === deselectEventType ) {
 					deselect();
 				}
 			}
diff --git src/wp-includes/js/tinymce/skins/wordpress/images/dashicon-edit.png src/wp-includes/js/tinymce/skins/wordpress/images/dashicon-edit.png
new file mode 100755
index 0000000..eea51cb
Binary files /dev/null and src/wp-includes/js/tinymce/skins/wordpress/images/dashicon-edit.png differ
diff --git src/wp-includes/js/tinymce/skins/wordpress/images/dashicon-no-alt.png src/wp-includes/js/tinymce/skins/wordpress/images/dashicon-no-alt.png
new file mode 100755
index 0000000..90c8ef7
Binary files /dev/null and src/wp-includes/js/tinymce/skins/wordpress/images/dashicon-no-alt.png differ
diff --git src/wp-includes/js/tinymce/skins/wordpress/wp-content.css src/wp-includes/js/tinymce/skins/wordpress/wp-content.css
index fe84a39..ee54c33 100644
--- src/wp-includes/js/tinymce/skins/wordpress/wp-content.css
+++ src/wp-includes/js/tinymce/skins/wordpress/wp-content.css
@@ -204,6 +204,11 @@ audio {
 	width: 100%;
 }
 
+.ie8 .wpview-wrap .wpview-clipboard,
+.ie7 .wpview-wrap .wpview-clipboard {
+	filter: alpha(opacity=0);
+}
+
 /**
  * Media previews
  */
@@ -214,12 +219,18 @@ audio {
 }
 
 .wpview-wrap.selected {
-	background-color: #f2f8ff; /* fallback to old blue */
+	background-color: #e5e5e5;
 	background-color: rgba(0,0,0,0.1);
 	border-color: #777;
 	border-color: rgba(0,0,0,0.3);
 }
 
+.ie8 .wpview-wrap.selected,
+.ie7 .wpview-wrap.selected {
+	background-color: #e5e5e5;
+	border-color: #777;
+}
+
 .wpview-overlay {
 	position: absolute;
 	top: 0;
@@ -263,6 +274,25 @@ audio {
 	font-size: 30px;
 }
 
+.ie8 .wpview-wrap .toolbar div,
+.ie7 .wpview-wrap .toolbar div,
+.ie8 #wp-image-toolbar div,
+.ie7 #wp-image-toolbar div {
+	display: inline;
+	padding: 0;
+}
+
+.ie8 .dashicons-edit,
+.ie7 .dashicons-edit {
+	background-image: url(images/dashicon-edit.png);
+}
+
+.ie8 .dashicons-no-alt,
+.ie7 .dashicons-no-alt {
+	background-image: url(images/dashicon-no-alt.png);
+}
+
+
 .wpview-wrap .toolbar div:hover,
 #wp-image-toolbar div:hover {
 	box-shadow: 0 1px 3px rgba(0,0,0,0.8);
@@ -352,6 +382,11 @@ audio {
 	box-sizing: border-box;
 }
 
+.ie7 .gallery .gallery-item,
+.ie8 .gallery .gallery-item {
+	padding: 6px 0;
+}
+
 .gallery .gallery-caption,
 .gallery .gallery-icon {
 	margin: 0;
@@ -374,6 +409,11 @@ audio {
 	width: 33.333%;
 }
 
+.ie8 .gallery-columns-3 .gallery-item,
+.ie7 .gallery-columns-3 .gallery-item {
+	width: 33%;
+}
+
 .gallery-columns-4 .gallery-item {
 	width: 25%;
 }