Index: wp-includes/js/plupload/handlers.dev.js
===================================================================
--- wp-includes/js/plupload/handlers.dev.js	(revision 19011)
+++ wp-includes/js/plupload/handlers.dev.js	(working copy)
@@ -24,6 +24,11 @@
 	jQuery('#cancel-upload').prop('disabled', false);
 }
 
+// see if the file is in the queue
+function fileIsQueued(fileObj) {
+	return 1 == jQuery('#media-item-' + fileObj.id ,jQuery('#media-items')).length;
+}
+
 function uploadStart(fileObj) {
 	try {
 		if ( typeof topWin.tb_remove != 'undefined' )
@@ -435,6 +440,8 @@
 		});
 
 		uploader.bind('Error', function(up, err) {
+			if ( !fileIsQueued(err.file) )
+				fileQueued(err.file);
 			uploadError(err.file, err.code, err.message);
 
 			up.refresh();