diff --git src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js
index 3ba19b4..63afb3a 100644
--- src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js
+++ src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js
@@ -102,7 +102,7 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 			});
 
 			if ( out.indexOf('[caption') !== 0 ) {
-				// the caption html seems brocken, try to find the image that may be wrapped in a link
+				// the caption html seems broken, try to find the image that may be wrapped in a link
 				// and may be followed by <p> with the caption text.
 				out = b.replace( /[\s\S]*?((?:<a [^>]+>)?<img [^>]+>(?:<\/a>)?)(<p>[\s\S]*<\/p>)?[\s\S]*/gi, '<p>$1</p>$2' );
 			}
@@ -339,6 +339,7 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 		} else {
 			editor.dom.remove( node );
 		}
+		removeToolbar();
 	}
 
 	function addToolbar( node ) {
@@ -755,9 +756,10 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 			selection = editor.selection,
 			dom = editor.dom;
 
+		node = selection.getNode();
+
 		if ( event.keyCode === tinymce.util.VK.ENTER ) {
 			// When pressing Enter inside a caption move the caret to a new parapraph under it
-			node = selection.getNode();
 			wrap = dom.getParent( node, 'div.mceTemp' );
 
 			if ( wrap ) {
@@ -783,7 +785,6 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 				selection.setCursorLocation( P, 0 );
 			}
 		} else if ( event.keyCode === tinymce.util.VK.DELETE || event.keyCode === tinymce.util.VK.BACKSPACE ) {
-			node = selection.getNode();
 
 			if ( node.nodeName === 'DIV' && dom.hasClass( node, 'mceTemp' ) ) {
 				wrap = node;
@@ -797,6 +798,11 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 				return false;
 			}
 		}
+
+		// Key presses will replace the image so we need to remove the toolbar
+		if ( dom.getAttrib( node, 'data-wp-imgselect' ) ) {
+			removeToolbar();
+		}
 	});
 
 	editor.on( 'mousedown', function( event ) {
@@ -828,7 +834,6 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 
 				if ( dom.hasClass( node, 'remove' ) ) {
 					removeImage( image );
-					removeToolbar();
 				} else if ( dom.hasClass( node, 'edit' ) ) {
 					editImage( image );
 				}