diff --git a/src/wp-includes/js/media-editor.js b/src/wp-includes/js/media-editor.js
index fdf27bb319..ee1389a264 100644
--- a/src/wp-includes/js/media-editor.js
+++ b/src/wp-includes/js/media-editor.js
@@ -583,7 +583,7 @@
 				style: 'light',
 				tracklist: false,
 				tracknumbers: false,
-				images: false
+				images: true
 			}
 		};
 
@@ -812,10 +812,16 @@
 			}, this );
 
 			workflow.state('playlist-edit').on( 'update', function( selection ) {
+				/**
+				 * @this wp.media.editor
+				 */
 				this.insert( wp.media.playlist.shortcode( selection ).string() );
 			}, this );
 
 			workflow.state('video-playlist-edit').on( 'update', function( selection ) {
+				/**
+				 * @this wp.media.editor
+				 */
 				this.insert( wp.media['video-playlist'].shortcode( selection ).string() );
 			}, this );
 
diff --git a/src/wp-includes/media-template.php b/src/wp-includes/media-template.php
index 14b1cff580..daf8c29911 100644
--- a/src/wp-includes/media-template.php
+++ b/src/wp-includes/media-template.php
@@ -431,24 +431,35 @@ function wp_print_media_templates() {
 			</select>
 		</label>
 
+		<#
+			var playlist = 'playlist-edit' === data.controller.id, emptyModel = 'undefined' === typeof data.model.style;
+		#>
 		<label class="setting">
 			<span><?php _e( 'Show Tracklist' ); ?></span>
-			<input type="checkbox" data-setting="_tracklist" />
+			<input type="checkbox" data-setting="_tracklist" <# if ( playlist && emptyModel ) { #>
+				checked="checked"
+			<# } #> />
 		</label>
 
 		<label class="setting">
 			<span><?php _e( 'Show Track Numbers' ); ?></span>
-			<input type="checkbox" data-setting="_tracknumbers" />
+			<input type="checkbox" data-setting="_tracknumbers" <# if ( playlist && emptyModel ) { #>
+				checked="checked"
+			<# } #> />
 		</label>
 
 		<label class="setting">
 			<span><?php _e( 'Show Artist Name in Tracklist' ); ?></span>
-			<input type="checkbox" data-setting="_artists" />
+			<input type="checkbox" data-setting="_artists" <# if ( playlist && emptyModel ) { #>
+				checked="checked"
+			<# } #> />
 		</label>
 
 		<label class="setting">
 			<span><?php _e( 'Show Images' ); ?></span>
-			<input type="checkbox" data-setting="_images" />
+			<input type="checkbox" data-setting="_images" <# if ( emptyModel ) { #>
+				checked="checked"
+			<# } #> />
 		</label>
 	</script>