diff --git a/src/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js b/src/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js
index d68904afb1..5f3ff1a827 100644
--- a/src/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js
+++ b/src/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js
@@ -62,15 +62,14 @@
 			if ( event.keyCode === VK.ENTER && ! VK.modifierPressed( event ) ) {
 				enter();
 			}
-		}, true );
 
-		editor.on( 'keyup', function( event ) {
+			// Wait for the browser to insert the character.
 			if ( event.keyCode === VK.SPACEBAR && ! event.ctrlKey && ! event.metaKey && ! event.altKey ) {
-				space();
+				setTimeout( space );
 			} else if ( event.keyCode > 47 && ! ( event.keyCode >= 91 && event.keyCode <= 93 ) ) {
-				inline();
+				setTimeout( inline );
 			}
-		} );
+		}, true );
 
 		function inline() {
 			var rng = editor.selection.getRng();
diff --git a/tests/qunit/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js b/tests/qunit/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js
index edcb629876..73ba48b00d 100644
--- a/tests/qunit/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js
+++ b/tests/qunit/wp-includes/js/tinymce/plugins/wptextpattern/plugin.js
@@ -6,7 +6,7 @@
 		return;
 	}
 
-	function mceType(chr) {
+	function mceType( chr, noKeyUp ) {
 		var editor = tinymce.activeEditor, keyCode, charCode, evt, startElm, rng, startContainer, startOffset, textNode;
 
 		function charCodeToKeyCode(charCode) {
@@ -109,12 +109,17 @@
 			}
 		}
 
-		fakeEvent(startElm, 'keyup', evt);
+		if ( ! noKeyUp ) {
+			fakeEvent(startElm, 'keyup', evt);
+		}
 	}
 
 	function type() {
 		var args = arguments;
 
+		// Wait once for conversions to be triggered,
+		// and once for the `canUndo` flag to be set.
+		setTimeout( function() {
 		setTimeout( function() {
 			if ( typeof args[0] === 'string' ) {
 				args[0] = args[0].split( '' );
@@ -134,6 +139,7 @@
 				type.apply( null, args );
 			}
 		} );
+		} );
 	}
 
 	QUnit.module( 'tinymce.plugins.wptextpattern', {
@@ -177,6 +183,14 @@
 		}, assert.async() );
 	} );
 
+	QUnit.test( 'Unordered list. (fast)', function( assert ) {
+		type( '*', function() {
+			mceType( ' ', true );
+		}, 'a', function() {
+			assert.equal( editor.getContent(), '<ul>\n<li>a</li>\n</ul>' );
+		}, assert.async() );
+	} );
+
 	QUnit.test( 'Ordered list.', function( assert ) {
 		type( '1. a', function() {
 			assert.equal( editor.getContent(), '<ol>\n<li>a</li>\n</ol>' );