diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-extension.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-extension.ts
index 3f8bbdee192e..154a68377b82 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-extension.ts
@@ -47,8 +47,35 @@ export const HtmlClassAttribute = Extension.create<UmbTiptapHtmlClassAttributeOp
 				({ commands, editor }) => {
 					if (!className) return false;
 					const types = type ? [type] : this.options.types;
-					const existing = types.map((type) => editor.getAttributes(type)?.class as string).filter((x) => x);
-					return existing.length ? commands.unsetClassName(type) : commands.setClassName(className, type);
+
+					const toggleClasses = className.split(/\s+/).filter((c) => c);
+					if (toggleClasses.length === 0) {
+						return true;
+					}
+
+					return types
+						.map((t) => {
+							const existingClass = (editor.getAttributes(t)?.class as string) ?? '';
+							const classes = existingClass.split(/\s+/).filter((c) => c);
+							const hasAllToggleClasses = toggleClasses.every((c) => classes.includes(c));
+
+							let newClasses: Array<string>;
+							if (hasAllToggleClasses) {
+								// All toggle classes present: remove them
+								newClasses = classes.filter((c) => !toggleClasses.includes(c));
+							} else {
+								// Not all toggle classes present: add missing ones
+								const toAdd = toggleClasses.filter((c) => !classes.includes(c));
+								newClasses = [...classes, ...toAdd];
+							}
+
+							if (newClasses.length === 0) {
+								// No classes left, remove the attribute entirely
+								return commands.resetAttributes(t, 'class');
+							}
+							return commands.updateAttributes(t, { class: newClasses.join(' ') });
+						})
+						.every((response) => response);
 				},
 			unsetClassName:
 				(type) =>
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-extension.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-extension.ts
index 0384aa3ed66f..f70da6631897 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-extension.ts
@@ -33,6 +33,20 @@ export const UmbLink = Link.extend({
 
 	addCommands() {
 		return {
+			// TODO: [v17] Remove the `@ts-expect-error` once Tiptap has resolved the TypeScript definitions. [LK:2025-10-01]
+			// eslint-disable-next-line @typescript-eslint/ban-ts-comment
+			// @ts-expect-error
+			ensureUmbLink: (attributes) => {
+				// TODO: [v17] Remove the `@ts-expect-error` once Tiptap has resolved the TypeScript definitions. [LK:2025-10-01]
+				// eslint-disable-next-line @typescript-eslint/ban-ts-comment
+				// @ts-expect-error
+				return ({ editor, chain }) => {
+					if (editor.isActive(this.name)) {
+						return true;
+					}
+					return chain().setMark(this.name, attributes).setMeta('preventAutolink', true).run();
+				};
+			},
 			// TODO: [v17] Remove the `@ts-expect-error` once Tiptap has resolved the TypeScript definitions. [LK:2025-10-01]
 			// eslint-disable-next-line @typescript-eslint/ban-ts-comment
 			// @ts-expect-error
@@ -59,6 +73,14 @@ export const UmbLink = Link.extend({
 declare module '@tiptap/core' {
 	interface Commands<ReturnType> {
 		umbLink: {
+			ensureUmbLink: (attributes: {
+				type: string;
+				href: string;
+				'data-anchor'?: string | null;
+				target?: string | null;
+				title?: string | null;
+			}) => ReturnType;
+
 			setUmbLink: (attributes: {
 				type: string;
 				href: string;
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts
index f3b991cb4959..f73fa051eec7 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts
@@ -4,7 +4,7 @@ import type { ChainedCommands, Editor } from '../../externals.js';
 
 type UmbTiptapToolbarStyleMenuCommandType = {
 	type: string;
-	command: (chain: ChainedCommands) => ChainedCommands;
+	command?: (chain: ChainedCommands) => ChainedCommands;
 	isActive?: (editor?: Editor) => boolean | undefined;
 };
 
@@ -25,6 +25,7 @@ export default class UmbTiptapToolbarStyleMenuApi extends UmbTiptapToolbarElemen
 		h5: this.#headingCommand(5),
 		h6: this.#headingCommand(6),
 		p: { type: 'paragraph', command: (chain) => chain.setParagraph() },
+		a: { type: 'umbLink', command: (chain) => chain.ensureUmbLink({ type: 'external', href: '#' }) },
 		blockquote: { type: 'blockquote', command: (chain) => chain.toggleBlockquote() },
 		code: { type: 'code', command: (chain) => chain.toggleCode() },
 		codeBlock: { type: 'codeBlock', command: (chain) => chain.toggleCodeBlock() },