diff --git a/src/Umbraco.Web.UI.Client/src/packages/multi-url-picker/tiny-mce-plugin/tiny-mce-multi-url-picker.plugin.ts b/src/Umbraco.Web.UI.Client/src/packages/multi-url-picker/tiny-mce-plugin/tiny-mce-multi-url-picker.plugin.ts
index c8591199fd..74442fba55 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/multi-url-picker/tiny-mce-plugin/tiny-mce-multi-url-picker.plugin.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/multi-url-picker/tiny-mce-plugin/tiny-mce-multi-url-picker.plugin.ts
@@ -30,16 +30,24 @@ export default class UmbTinyMceMultiUrlPickerPlugin extends UmbTinyMcePluginBase
 		// 	return () => editor.off('NodeChange', editorEventCallback);
 		// };
 
-		args.editor.ui.registry.addButton('link', {
+		this.editor.ui.registry.addToggleButton('link', {
 			icon: 'link',
 			tooltip: 'Insert/edit link',
 			onAction: () => this.showDialog(),
+			onSetup: (api) => {
+				const changed = this.editor.selection.selectorChangedWithUnbind('a', (state) => api.setActive(state));
+				return () => changed.unbind();
+			},
 		});
 
-		args.editor.ui.registry.addButton('unlink', {
+		this.editor.ui.registry.addToggleButton('unlink', {
 			icon: 'unlink',
-			tooltip: 'Remove link',
+			tooltip: 'Remove Link',
 			onAction: () => args.editor.execCommand('unlink'),
+			onSetup: (api) => {
+				const changed = this.editor.selection.selectorChangedWithUnbind('a', (state) => api.setActive(state));
+				return () => changed.unbind();
+			},
 		});
 	}
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiny-mce/plugins/tiny-mce-embeddedmedia.plugin.ts b/src/Umbraco.Web.UI.Client/src/packages/tiny-mce/plugins/tiny-mce-embeddedmedia.plugin.ts
index 1cadeaa0fe..890510b11b 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiny-mce/plugins/tiny-mce-embeddedmedia.plugin.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiny-mce/plugins/tiny-mce-embeddedmedia.plugin.ts
@@ -10,17 +10,11 @@ export default class UmbTinyMceEmbeddedMediaPlugin extends UmbTinyMcePluginBase
 			icon: 'embed',
 			tooltip: 'Embed',
 			onAction: () => this.#onAction(),
-			onSetup: (api) => {
-				const editor = this.editor;
-				const onNodeChange = () => {
-					const selectedElm = editor.selection.getNode();
-					api.setActive(
-						selectedElm.nodeName.toUpperCase() === 'DIV' && selectedElm.classList.contains('umb-embed-holder'),
-					);
-				};
-
-				editor.on('NodeChange', onNodeChange);
-				return () => editor.off('NodeChange', onNodeChange);
+			onSetup: function (api) {
+				const changed = args.editor.selection.selectorChangedWithUnbind('div.umb-embed-holder', (state) =>
+					api.setActive(state),
+				);
+				return () => changed.unbind();
 			},
 		});
 	}