diff --git a/src/wp-includes/css/editor.css b/src/wp-includes/css/editor.css
index 4e3bf348c3..af2d901e59 100644
--- a/src/wp-includes/css/editor.css
+++ b/src/wp-includes/css/editor.css
@@ -174,6 +174,7 @@ div.mce-inline-toolbar-grp {
 	-webkit-user-select: none;
 	-ms-user-select: none;
 	user-select: none;
+	max-width: 98%;
 	z-index: 100100; /* Same as the other TinyMCE "panels" */
 }
 
@@ -1602,6 +1603,9 @@ i.mce-i-wp_code:before {
 .wp-link-preview {
 	float: left;
 	margin: 5px;
+	max-width: 694px;
+	overflow: hidden;
+	text-overflow: ellipsis;
 }
 
 .wp-link-preview a {
@@ -1616,6 +1620,14 @@ i.mce-i-wp_code:before {
 	cursor: pointer;
 }
 
+@media screen and ( max-width: 782px ) {
+	.wp-link-preview {
+		max-width: 70%;
+		max-width: -webkit-calc(100% - 88px);
+		max-width: calc(100% - 88px);
+	}
+}
+
 /* =Overlay Body
 -------------------------------------------------------------- */
 
diff --git a/src/wp-includes/js/tinymce/plugins/wplink/plugin.js b/src/wp-includes/js/tinymce/plugins/wplink/plugin.js
index 419c1cf622..ffecb967b2 100644
--- a/src/wp-includes/js/tinymce/plugins/wplink/plugin.js
+++ b/src/wp-includes/js/tinymce/plugins/wplink/plugin.js
@@ -80,12 +80,18 @@ tinymce.PluginManager.add( 'wplink', function( editor ) {
 
 				url = url.replace( /(?:index)?\.html$/, '' );
 
-				if ( ( lastIndex = url.lastIndexOf( '/' ) ) === url.length - 1 ) {
-					url = url.slice( 0, lastIndex );
+				if ( url.charAt( url.length - 1 ) === '/' ) {
+					url = url.slice( 0, -1 );
 				}
 
-				if ( ( index = url.indexOf( '/' ) ) !== -1 && ( lastIndex = url.lastIndexOf( '/' ) ) !== -1 && lastIndex !== index ) {
-					url = url.slice( 0, index + 1 ) + '\u2026' + url.slice( lastIndex, url.length );
+				// If the URL is longer that 40 chars, concatenate the beginning (after the domain) and ending with ...
+				if ( url.length > 40 && ( index = url.indexOf( '/' ) ) !== -1 && ( lastIndex = url.lastIndexOf( '/' ) ) !== -1 && lastIndex !== index ) {
+					// If the beginning + ending are shorter that 40 chars, show more of the ending
+					if ( index + url.length - lastIndex < 40 ) {
+						lastIndex =  -( 40 - ( index + 1 ) );
+					}
+
+					url = url.slice( 0, index + 1 ) + '\u2026' + url.slice( lastIndex );
 				}
 
 				tinymce.$( this.getEl().firstChild ).attr( 'href', this.url ).text( url );
@@ -96,11 +102,13 @@ tinymce.PluginManager.add( 'wplink', function( editor ) {
 
 			editor.on( 'wptoolbar', function( event ) {
 				var anchor = editor.dom.getParent( event.element, 'a' ),
+					$ = editor.$,
 					href;
 
-				if ( anchor && ( href = editor.$( anchor ).attr( 'href' ) ) ) {
-					self.setURL( href );
+				if ( anchor && ! $( anchor ).find( 'img' ).length &&
+					( href = $( anchor ).attr( 'href' ) ) ) {
 
+					self.setURL( href );
 					event.element = anchor;
 					event.toolbar = toolbar;
 				}