diff --git a/wp-admin/js/media-upload.js b/wp-admin/js/media-upload.js
index caf609de44..4713d068a1 100644
--- a/wp-admin/js/media-upload.js
+++ b/wp-admin/js/media-upload.js
@@ -108,9 +108,12 @@ var tb_position;
 			} ) );
 
 			workflow.on( 'update:insert', function( selection ) {
-				this.insert( '\n' + selection.map( function( attachment ) {
-					return wp.media.string.image( attachment );
-				}).join('\n\n') + '\n' );
+				this.insert( selection.map( function( attachment ) {
+					if ( 'image' === attachment.get('type') )
+						return '\n' + wp.media.string.image( attachment ) + '\n';
+					else
+						return wp.media.string.link( attachment ) + ' ';
+				}).join('') );
 			}, this );
 
 			workflow.on( 'update:gallery', function( selection ) {
diff --git a/wp-includes/js/mce-view.js b/wp-includes/js/mce-view.js
index 0c88864d2e..88425e0a8c 100644
--- a/wp-includes/js/mce-view.js
+++ b/wp-includes/js/mce-view.js
@@ -371,6 +371,24 @@ window.wp = window.wp || {};
 	var mceview = wp.mce.view;
 
 	wp.media.string = {};
+
+	wp.media.string.link = function( attachment ) {
+		var linkTo  = getUserSetting( 'urlbutton', 'post' ),
+			options = {
+				tag:     'a',
+				content: attachment.get('title') || attachment.get('filename'),
+				attrs:   {
+					rel: 'attachment wp-att-' + attachment.id
+				}
+			};
+
+		// Attachments can be linked to attachment post pages or to the direct
+		// URL. `none` is not a valid option.
+		options.attrs.href = ( linkTo === 'file' ) ? attachment.get('url') : attachment.get('link');
+
+		return wp.html.string( options );
+	};
+
 	wp.media.string.image = function( attachment, props ) {
 		var classes, img, options, size;
 
diff --git a/wp-includes/media.php b/wp-includes/media.php
index 6d72e3d30b..87762f7de2 100644
--- a/wp-includes/media.php
+++ b/wp-includes/media.php
@@ -1246,6 +1246,7 @@ function wp_prepare_attachment_for_js( $attachment ) {
 		'title'       => $attachment->post_title,
 		'filename'    => basename( $attachment->guid ),
 		'url'         => $attachment_url,
+		'link'        => get_attachment_link( $attachment->ID ),
 		'alt'         => get_post_meta( $attachment->ID, '_wp_attachment_image_alt', true ),
 		'author'      => $attachment->post_author,
 		'description' => $attachment->post_content,