diff --git a/src/Umbraco.Web.UI.Client/package-lock.json b/src/Umbraco.Web.UI.Client/package-lock.json
index 1e44328da800..d3ed09bef38a 100644
--- a/src/Umbraco.Web.UI.Client/package-lock.json
+++ b/src/Umbraco.Web.UI.Client/package-lock.json
@@ -17064,17 +17064,36 @@
 			"name": "@umbraco-backoffice/external-tiptap",
 			"dependencies": {
 				"@tiptap/core": "2.26.1",
+				"@tiptap/extension-blockquote": "2.26.1",
+				"@tiptap/extension-bold": "2.26.1",
+				"@tiptap/extension-bullet-list": "2.26.1",
 				"@tiptap/extension-character-count": "2.26.1",
+				"@tiptap/extension-code": "2.26.1",
+				"@tiptap/extension-code-block": "2.26.1",
+				"@tiptap/extension-document": "2.26.1",
+				"@tiptap/extension-dropcursor": "2.26.1",
+				"@tiptap/extension-gapcursor": "2.26.1",
+				"@tiptap/extension-hard-break": "2.26.1",
+				"@tiptap/extension-heading": "2.26.1",
+				"@tiptap/extension-history": "2.26.1",
+				"@tiptap/extension-horizontal-rule": "2.26.1",
 				"@tiptap/extension-image": "2.26.1",
+				"@tiptap/extension-italic": "2.26.1",
 				"@tiptap/extension-link": "2.26.1",
+				"@tiptap/extension-list-item": "2.26.1",
+				"@tiptap/extension-ordered-list": "2.26.1",
+				"@tiptap/extension-paragraph": "2.26.1",
 				"@tiptap/extension-placeholder": "2.26.1",
+				"@tiptap/extension-strike": "2.26.1",
 				"@tiptap/extension-subscript": "2.26.1",
 				"@tiptap/extension-superscript": "2.26.1",
 				"@tiptap/extension-table": "2.26.1",
 				"@tiptap/extension-table-cell": "2.26.1",
 				"@tiptap/extension-table-header": "2.26.1",
 				"@tiptap/extension-table-row": "2.26.1",
+				"@tiptap/extension-text": "2.26.1",
 				"@tiptap/extension-text-align": "2.26.1",
+				"@tiptap/extension-text-style": "2.26.1",
 				"@tiptap/extension-underline": "2.26.1",
 				"@tiptap/pm": "2.26.1",
 				"@tiptap/starter-kit": "2.26.1"
diff --git a/src/Umbraco.Web.UI.Client/src/assets/lang/en.ts b/src/Umbraco.Web.UI.Client/src/assets/lang/en.ts
index d4806a5f1bad..4fd053f1522c 100644
--- a/src/Umbraco.Web.UI.Client/src/assets/lang/en.ts
+++ b/src/Umbraco.Web.UI.Client/src/assets/lang/en.ts
@@ -2792,6 +2792,7 @@ export default {
 		config_statusbar: 'Statusbar',
 		config_toolbar: 'Toolbar',
 		extGroup_formatting: 'Text formatting',
+		extGroup_html: 'HTML',
 		extGroup_interactive: 'Interactive elements',
 		extGroup_media: 'Embeds and media',
 		extGroup_structure: 'Content structure',
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-anchor.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-anchor.extension.ts
index 12c5a2b0ecef..fda5a77bfcba 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-anchor.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-anchor.extension.ts
@@ -1,5 +1,6 @@
 import { Node, mergeAttributes } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const Anchor = Node.create({
 	name: 'anchor',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-div.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-div.extension.ts
index e7855d428879..374acf255777 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-div.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-div.extension.ts
@@ -1,5 +1,6 @@
 import { Node, mergeAttributes } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface DivOptions {
 	/**
 	 * HTML attributes to add to the element.
@@ -9,6 +10,7 @@ export interface DivOptions {
 	HTMLAttributes: Record<string, any>;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const Div = Node.create<DivOptions>({
 	name: 'div',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figcaption.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figcaption.extension.ts
index ea2f2ab83e7f..8a1bce8d409e 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figcaption.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figcaption.extension.ts
@@ -1,5 +1,6 @@
 import { Node } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface FigcaptionOptions {
 	/**
 	 * HTML attributes to add to the image element.
@@ -9,6 +10,7 @@ export interface FigcaptionOptions {
 	HTMLAttributes: Record<string, any>;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const Figcaption = Node.create<FigcaptionOptions>({
 	name: 'figcaption',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figure.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figure.extension.ts
index 49a89606dfab..4e4b67a3081a 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figure.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-figure.extension.ts
@@ -1,5 +1,6 @@
 import { mergeAttributes, Node } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface FigureOptions {
 	/**
 	 * HTML attributes to add to the image element.
@@ -9,6 +10,7 @@ export interface FigureOptions {
 	HTMLAttributes: Record<string, any>;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const Figure = Node.create<FigureOptions>({
 	name: 'figure',
 	group: 'block',
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-html-global-attributes.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-html-global-attributes.extension.ts
index 69c0cbdd1f89..06454f82b9e8 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-html-global-attributes.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-html-global-attributes.extension.ts
@@ -10,6 +10,7 @@ function camelCaseToKebabCase(str: string): string {
 	return str.replace(/[A-Z]+(?![a-z])|[A-Z]/g, ($, ofs) => (ofs ? '-' : '') + $.toLowerCase());
 }
 
+/** @deprecated No longer used internally. This will be removed in Umbraco 17. [LK] */
 export interface HtmlGlobalAttributesOptions {
 	/**
 	 * The types where the text align attribute can be applied.
@@ -19,6 +20,7 @@ export interface HtmlGlobalAttributesOptions {
 	types: Array<string>;
 }
 
+/** @deprecated No longer used internally. This will be removed in Umbraco 17. [LK] */
 export const HtmlGlobalAttributes = Extension.create<HtmlGlobalAttributesOptions>({
 	name: 'htmlGlobalAttributes',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-span.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-span.extension.ts
index e0adabf8af71..bee0cd8632df 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-span.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-span.extension.ts
@@ -1,5 +1,6 @@
 import { Mark, mergeAttributes } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface SpanOptions {
 	/**
 	 * HTML attributes to add to the span element.
@@ -34,6 +35,7 @@ function serializeStyles(items: Record<string, string>): string {
 	);
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const Span = Mark.create<SpanOptions>({
 	name: 'span',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-direction-extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-direction-extension.ts
index 914d151cd1f2..96727e9dae23 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-direction-extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-direction-extension.ts
@@ -1,10 +1,12 @@
 import { Extension } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface TextDirectionOptions {
 	directions: Array<'auto' | 'ltr' | 'rtl'>;
 	types: Array<string>;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const TextDirection = Extension.create<TextDirectionOptions>({
 	name: 'textDirection',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-indent-extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-indent-extension.ts
index 7df5d4043e2b..a39c10605d28 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-indent-extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-text-indent-extension.ts
@@ -11,12 +11,14 @@ import type { EditorState, Transaction } from '@tiptap/pm/state';
 import { Extension } from '@tiptap/core';
 import { AllSelection, TextSelection } from '@tiptap/pm/state';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface TextIndentOptions {
 	minLevel: number;
 	maxLevel: number;
 	types: Array<string>;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const TextIndent = Extension.create<TextIndentOptions>({
 	name: 'textIndent',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-trailing-node.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-trailing-node.extension.ts
index f76956fa9013..ec7f4144f1c5 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-trailing-node.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-trailing-node.extension.ts
@@ -13,11 +13,13 @@ function nodeEqualsType({ types, node }) {
 	return (Array.isArray(types) && types.includes(node.type)) || node.type === types;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface TrailingNodeOptions {
 	node: string;
 	notAfter: string[];
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const TrailingNode = Extension.create<TrailingNodeOptions>({
 	name: 'trailingNode',
 
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-bubble-menu.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-bubble-menu.extension.ts
index f2b080c42ef1..a34064ae9ce6 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-bubble-menu.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-bubble-menu.extension.ts
@@ -5,11 +5,13 @@ import { EditorState, Plugin, PluginKey } from '@tiptap/pm/state';
 import { EditorView } from '@tiptap/pm/view';
 import type { PluginView } from '@tiptap/pm/state';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface UmbTiptapBubbleMenuElement extends HTMLElement {
 	editor?: Editor;
 	menuAlias?: string;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export type UmbBubbleMenuPluginProps = {
 	unique: string;
 	placement?: UUIPopoverContainerElement['placement'];
@@ -20,8 +22,10 @@ export type UmbBubbleMenuPluginProps = {
 		| null;
 };
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export type UmbBubbleMenuOptions = UmbBubbleMenuPluginProps;
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbBubbleMenu = Extension.create<UmbBubbleMenuOptions>({
 	name: 'umbBubbleMenu',
 
@@ -104,6 +108,7 @@ class UmbBubbleMenuPluginView implements PluginView {
 	}
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbBubbleMenuPlugin = (editor: Editor, props: UmbBubbleMenuPluginProps) => {
 	return new Plugin({
 		view(editorView) {
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-embedded-media.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-embedded-media.extension.ts
index daecec24689c..fce7c67a4863 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-embedded-media.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-embedded-media.extension.ts
@@ -1,9 +1,11 @@
 import { mergeAttributes, Node } from '@tiptap/core';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface UmbEmbeddedMediaOptions {
 	inline: boolean;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const umbEmbeddedMedia = Node.create<UmbEmbeddedMediaOptions>({
 	name: 'umbEmbeddedMedia',
 	group() {
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-image.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-image.extension.ts
index 84acd5b11d6c..1f91f7e95829 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-image.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-image.extension.ts
@@ -1,5 +1,6 @@
 import Image from '@tiptap/extension-image';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export interface UmbImageAttributes {
 	src: string;
 	alt?: string;
@@ -13,6 +14,7 @@ export interface UmbImageAttributes {
 	'data-udi'?: string;
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbImage = Image.extend({
 	addAttributes() {
 		return {
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-link.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-link.extension.ts
index 9ba943399359..ef7e66617ed3 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-link.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-link.extension.ts
@@ -1,5 +1,6 @@
 import Link from '@tiptap/extension-link';
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbLink = Link.extend({
 	name: 'umbLink',
 
@@ -12,6 +13,9 @@ export const UmbLink = Link.extend({
 		};
 	},
 
+	// TODO: [LK] Look to use a NodeView to render the link
+	// https://tiptap.dev/docs/editor/extensions/custom-extensions/node-views/javascript
+
 	addOptions() {
 		return {
 			...this.parent?.(),
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-table.extension.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-table.extension.ts
index df5ec8a8fb30..a06850f07669 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-table.extension.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/extensions/tiptap-umb-table.extension.ts
@@ -12,6 +12,7 @@ import type { Rect } from '@tiptap/pm/tables';
 
 // NOTE: Custom TableView, to allow for custom styles to be applied to the <table> element. [LK]
 // ref: https://github.com/ueberdosis/tiptap/blob/v2.11.5/packages/extension-table/src/TableView.ts
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export class UmbTableView extends TableView {
 	constructor(node: ProseMirrorNode, cellMinWidth: number) {
 		super(node, cellMinWidth);
@@ -34,13 +35,16 @@ export class UmbTableView extends TableView {
 	}
 }
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbTable = Table.configure({ resizable: true, View: UmbTableView });
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbTableRow = TableRow.extend({
 	allowGapCursor: false,
 	content: '(tableCell | tableHeader)*',
 });
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbTableHeader = TableHeader.extend({
 	addAttributes() {
 		return {
@@ -122,6 +126,7 @@ export const UmbTableHeader = TableHeader.extend({
 	},
 });
 
+/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
 export const UmbTableCell = TableCell.extend({
 	addAttributes() {
 		return {
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/index.ts b/src/Umbraco.Web.UI.Client/src/external/tiptap/index.ts
index 9bb1aedd2892..1cfd0f26bde8 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/index.ts
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/index.ts
@@ -1,32 +1,134 @@
 // REQUIRED EXTENSIONS
 export * from '@tiptap/core';
-export { StarterKit } from '@tiptap/starter-kit';
-export { Placeholder } from '@tiptap/extension-placeholder';
-export { TextStyle } from '@tiptap/extension-text-style';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Document,
+} from '@tiptap/extension-document';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Dropcursor,
+} from '@tiptap/extension-dropcursor';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Gapcursor,
+} from '@tiptap/extension-gapcursor';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	HardBreak,
+} from '@tiptap/extension-hard-break';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	History,
+} from '@tiptap/extension-history';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Paragraph,
+} from '@tiptap/extension-paragraph';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Placeholder,
+} from '@tiptap/extension-placeholder';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Text,
+} from '@tiptap/extension-text';
 
 // OPTIONAL EXTENSIONS
-export { Blockquote } from '@tiptap/extension-blockquote';
-export { Bold } from '@tiptap/extension-bold';
-export { BulletList } from '@tiptap/extension-bullet-list';
-export { CharacterCount } from '@tiptap/extension-character-count';
-export { Code } from '@tiptap/extension-code';
-export { CodeBlock } from '@tiptap/extension-code-block';
-export { Heading } from '@tiptap/extension-heading';
-export { HorizontalRule } from '@tiptap/extension-horizontal-rule';
-export { Image } from '@tiptap/extension-image';
-export { Italic } from '@tiptap/extension-italic';
-export { Link } from '@tiptap/extension-link';
-export { ListItem } from '@tiptap/extension-list-item';
-export { OrderedList } from '@tiptap/extension-ordered-list';
-export { Strike } from '@tiptap/extension-strike';
-export { Subscript } from '@tiptap/extension-subscript';
-export { Superscript } from '@tiptap/extension-superscript';
-export { Table } from '@tiptap/extension-table';
-export { TableCell } from '@tiptap/extension-table-cell';
-export { TableHeader } from '@tiptap/extension-table-header';
-export { TableRow } from '@tiptap/extension-table-row';
-export { TextAlign } from '@tiptap/extension-text-align';
-export { Underline } from '@tiptap/extension-underline';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Blockquote,
+} from '@tiptap/extension-blockquote';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Bold,
+} from '@tiptap/extension-bold';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	BulletList,
+} from '@tiptap/extension-bullet-list';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	CharacterCount,
+} from '@tiptap/extension-character-count';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Code,
+} from '@tiptap/extension-code';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	CodeBlock,
+} from '@tiptap/extension-code-block';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Heading,
+} from '@tiptap/extension-heading';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	HorizontalRule,
+} from '@tiptap/extension-horizontal-rule';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Image,
+} from '@tiptap/extension-image';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Italic,
+} from '@tiptap/extension-italic';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Link,
+} from '@tiptap/extension-link';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	ListItem,
+} from '@tiptap/extension-list-item';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	OrderedList,
+} from '@tiptap/extension-ordered-list';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Strike,
+} from '@tiptap/extension-strike';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Subscript,
+} from '@tiptap/extension-subscript';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Superscript,
+} from '@tiptap/extension-superscript';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Table,
+} from '@tiptap/extension-table';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	TableCell,
+} from '@tiptap/extension-table-cell';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	TableHeader,
+} from '@tiptap/extension-table-header';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	TableRow,
+} from '@tiptap/extension-table-row';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	TextAlign,
+} from '@tiptap/extension-text-align';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	TextStyle,
+} from '@tiptap/extension-text-style';
+export {
+	/** @deprecated This will be relocated in Umbraco 17 to the "@umbraco-cms/backoffice/tiptap" module. [LK] */
+	Underline,
+} from '@tiptap/extension-underline';
+
+/** @deprecated No longer used internally. This will be removed in Umbraco 18. [LK] */
+export { StarterKit } from '@tiptap/starter-kit';
 
 // CUSTOM EXTENSIONS
 export * from './extensions/tiptap-anchor.extension.js';
diff --git a/src/Umbraco.Web.UI.Client/src/external/tiptap/package.json b/src/Umbraco.Web.UI.Client/src/external/tiptap/package.json
index 11938ce31a57..61a34ee1c9f5 100644
--- a/src/Umbraco.Web.UI.Client/src/external/tiptap/package.json
+++ b/src/Umbraco.Web.UI.Client/src/external/tiptap/package.json
@@ -7,10 +7,27 @@
 	},
 	"dependencies": {
 		"@tiptap/core": "2.26.1",
+		"@tiptap/extension-blockquote": "2.26.1",
+		"@tiptap/extension-bold": "2.26.1",
+		"@tiptap/extension-bullet-list": "2.26.1",
 		"@tiptap/extension-character-count": "2.26.1",
+		"@tiptap/extension-code-block": "2.26.1",
+		"@tiptap/extension-code": "2.26.1",
+		"@tiptap/extension-document": "2.26.1",
+		"@tiptap/extension-dropcursor": "2.26.1",
+		"@tiptap/extension-gapcursor": "2.26.1",
+		"@tiptap/extension-hard-break": "2.26.1",
+		"@tiptap/extension-heading": "2.26.1",
+		"@tiptap/extension-history": "2.26.1",
+		"@tiptap/extension-horizontal-rule": "2.26.1",
 		"@tiptap/extension-image": "2.26.1",
+		"@tiptap/extension-italic": "2.26.1",
 		"@tiptap/extension-link": "2.26.1",
+		"@tiptap/extension-list-item": "2.26.1",
+		"@tiptap/extension-ordered-list": "2.26.1",
+		"@tiptap/extension-paragraph": "2.26.1",
 		"@tiptap/extension-placeholder": "2.26.1",
+		"@tiptap/extension-strike": "2.26.1",
 		"@tiptap/extension-subscript": "2.26.1",
 		"@tiptap/extension-superscript": "2.26.1",
 		"@tiptap/extension-table": "2.26.1",
@@ -18,6 +35,8 @@
 		"@tiptap/extension-table-header": "2.26.1",
 		"@tiptap/extension-table-row": "2.26.1",
 		"@tiptap/extension-text-align": "2.26.1",
+		"@tiptap/extension-text-style": "2.26.1",
+		"@tiptap/extension-text": "2.26.1",
 		"@tiptap/extension-underline": "2.26.1",
 		"@tiptap/pm": "2.26.1",
 		"@tiptap/starter-kit": "2.26.1"
diff --git a/src/Umbraco.Web.UI.Client/src/packages/core/menu/components/menu-item/action/action-menu-item.api.ts b/src/Umbraco.Web.UI.Client/src/packages/core/menu/components/menu-item/action/action-menu-item.api.ts
index fc355cb98e8f..ea8daf334449 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/core/menu/components/menu-item/action/action-menu-item.api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/core/menu/components/menu-item/action/action-menu-item.api.ts
@@ -5,6 +5,11 @@ export abstract class UmbMenuItemActionApiBase<ArgsMetaType = never>
 	extends UmbActionBase<UmbMenuItemActionApiArgs<ArgsMetaType>>
 	implements UmbMenuItemActionApi<ArgsMetaType>
 {
+	/**
+	 * By specifying the `execute` method, the action will act as a button.
+	 * @abstract
+	 * @returns {Promise<void>}
+	 */
 	public execute(): Promise<void> {
 		return Promise.resolve();
 	}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/rte/components/rte-base.element.ts b/src/Umbraco.Web.UI.Client/src/packages/rte/components/rte-base.element.ts
index de1c417a04fd..ef841b82fcd0 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/rte/components/rte-base.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/rte/components/rte-base.element.ts
@@ -34,6 +34,8 @@ export abstract class UmbPropertyEditorUiRteElementBase
 	extends UmbFormControlMixin<UmbPropertyEditorRteValueType | undefined, typeof UmbLitElement, undefined>(UmbLitElement)
 	implements UmbPropertyEditorUiElement
 {
+	public name?: string;
+
 	public set config(config: UmbPropertyEditorConfigCollection | undefined) {
 		if (!config) return;
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/manifests.ts
deleted file mode 100644
index 99bbb4a2b52d..000000000000
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/manifests.ts
+++ /dev/null
@@ -1,11 +0,0 @@
-import { UMB_TIPTAP_ANCHOR_MODAL_ALIAS } from './constants.js';
-import type { ManifestModal } from '@umbraco-cms/backoffice/modal';
-
-export const manifests: Array<ManifestModal> = [
-	{
-		type: 'modal',
-		alias: UMB_TIPTAP_ANCHOR_MODAL_ALIAS,
-		name: 'Tiptap Anchor Modal',
-		element: () => import('./anchor-modal.element.js'),
-	},
-];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/index.ts
new file mode 100644
index 000000000000..ec606adf12fa
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/index.ts
@@ -0,0 +1 @@
+export * from './cascading-menu-popover.element.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/manifests.ts
deleted file mode 100644
index a238e84eb371..000000000000
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/manifests.ts
+++ /dev/null
@@ -1,11 +0,0 @@
-import { UMB_TIPTAP_CHARACTER_MAP_MODAL_ALIAS } from './constants.js';
-import type { ManifestModal } from '@umbraco-cms/backoffice/modal';
-
-export const manifests: Array<ManifestModal> = [
-	{
-		type: 'modal',
-		alias: UMB_TIPTAP_CHARACTER_MAP_MODAL_ALIAS,
-		name: 'Character Map Modal',
-		element: () => import('./character-map-modal.element.js'),
-	},
-];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/index.ts
index 56491b08d4aa..cc425ff2d0c8 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/index.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/index.ts
@@ -1,5 +1,3 @@
+export * from './cascading-menu-popover/index.js';
 export * from './input-tiptap/index.js';
-export * from './anchor-modal/index.js';
-export * from './cascading-menu-popover/cascading-menu-popover.element.js';
-export * from './character-map/index.js';
 export * from './menu/index.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/input-tiptap.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/input-tiptap.element.ts
index 0bb9fdbc66fe..03ef568b0939 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/input-tiptap.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/input-tiptap.element.ts
@@ -21,8 +21,8 @@ import type { CSSResultGroup } from '@umbraco-cms/backoffice/external/lit';
 import type { Extensions } from '@umbraco-cms/backoffice/external/tiptap';
 import type { UmbPropertyEditorConfigCollection } from '@umbraco-cms/backoffice/property-editor';
 
-import './tiptap-toolbar.element.js';
-import './tiptap-statusbar.element.js';
+import '../toolbar/tiptap-toolbar.element.js';
+import '../statusbar/tiptap-statusbar.element.js';
 
 const TIPTAP_CORE_EXTENSION_ALIAS = 'Umb.Tiptap.RichTextEssentials';
 
@@ -56,6 +56,9 @@ export class UmbInputTiptapElement extends UmbFormControlMixin<string, typeof Um
 	@property({ attribute: false })
 	configuration?: UmbPropertyEditorConfigCollection;
 
+	@property()
+	label?: string;
+
 	/**
 	 * Sets the input to required, meaning validation will fail if the value is empty.
 	 * @type {boolean}
@@ -114,7 +117,7 @@ export class UmbInputTiptapElement extends UmbFormControlMixin<string, typeof Um
 
 		// Ensures that the "Rich Text Essentials" extension is always enabled. [LK]
 		if (!enabledExtensions.includes(TIPTAP_CORE_EXTENSION_ALIAS)) {
-			const { api } = await import('../../extensions/core/rich-text-essentials.tiptap-api.js');
+			const { default: api } = await import('../../extensions/core/rich-text-essentials.tiptap-api.js');
 			this._extensions.push(new api(this));
 		}
 
@@ -124,7 +127,9 @@ export class UmbInputTiptapElement extends UmbFormControlMixin<string, typeof Um
 					if (manifest.api) {
 						const extension = await loadManifestApi(manifest.api);
 						if (extension) {
-							this._extensions.push(new extension(this));
+							const ext = new extension(this);
+							ext.manifest = manifest;
+							this._extensions.push(ext);
 						}
 					}
 				}
@@ -168,6 +173,7 @@ export class UmbInputTiptapElement extends UmbFormControlMixin<string, typeof Um
 		this._editor = new Editor({
 			element: element,
 			editable: !this.readonly,
+			editorProps: { attributes: { 'aria-label': this.label ?? 'Rich Text Editor' } },
 			extensions: tiptapExtensions,
 			content: this.#value,
 			injectCSS: false, // Prevents injecting CSS into `window.document`, as it never applies to the shadow DOM. [LK]
@@ -204,7 +210,7 @@ export class UmbInputTiptapElement extends UmbFormControlMixin<string, typeof Um
 			${repeat(
 				this.#stylesheets,
 				(stylesheet) => stylesheet,
-				(stylesheet) => html`<link rel="stylesheet" href="${stylesheet}" />`,
+				(stylesheet) => html`<link rel="stylesheet" href=${stylesheet} />`,
 			)}
 			<style>
 				${this._styles.map((style) => unsafeCSS(style))}
@@ -238,6 +244,11 @@ export class UmbInputTiptapElement extends UmbFormControlMixin<string, typeof Um
 		`;
 	}
 
+	override destroy(): void {
+		this._editor?.destroy();
+		this._editor = undefined;
+	}
+
 	static override readonly styles = [
 		css`
 			:host {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/manifests.ts
deleted file mode 100644
index 51a61448ef2e..000000000000
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/manifests.ts
+++ /dev/null
@@ -1,4 +0,0 @@
-import { manifests as anchorModal } from './anchor-modal/manifests.js';
-import { manifests as characterMap } from './character-map/manifests.js';
-
-export const manifests: Array<UmbExtensionManifest> = [...anchorModal, ...characterMap];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/menu/tiptap-menu.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/menu/tiptap-menu.element.ts
index cb6ba1624bdb..0e9068ab3a0e 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/menu/tiptap-menu.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/menu/tiptap-menu.element.ts
@@ -11,11 +11,11 @@ export class UmbTiptapMenuElement extends UmbMenuElement {
 		return html`
 			${when(
 				this.menuAlias || this.manifest?.alias,
-				(menu) => html`
+				(menuAlias) => html`
 					<umb-extension-with-api-slot
 						type="menuItem"
 						default-element="umb-action-menu-item"
-						.filter=${(items: ManifestMenuItem) => items.meta.menus.includes(menu)}></umb-extension-with-api-slot>
+						.filter=${(items: ManifestMenuItem) => items.meta.menus.includes(menuAlias)}></umb-extension-with-api-slot>
 				`,
 			)}
 		`;
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/tiptap-statusbar.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/statusbar/tiptap-statusbar.element.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/tiptap-statusbar.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/components/statusbar/tiptap-statusbar.element.ts
index 28293caa3761..83aba098b2c7 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/tiptap-statusbar.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/statusbar/tiptap-statusbar.element.ts
@@ -116,7 +116,7 @@ export class UmbTiptapStatusbarElement extends UmbLitElement {
 			box-sizing: border-box;
 
 			min-height: var(--uui-size-layout-1);
-			max-height: var(--uui-size-layout-2);
+			max-height: calc(var(--uui-size-layout-2) + var(--uui-size-1));
 
 			padding: 0 var(--uui-size-3);
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-button.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-button.element.ts
index 62cab87d772a..5360b665487d 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-button.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-button.element.ts
@@ -45,7 +45,7 @@ export class UmbTiptapToolbarButtonElement extends UmbLitElement {
 				look=${this.isActive ? 'outline' : 'default'}
 				label=${label}
 				title=${label}
-				?disabled=${this.api && this.editor && this.api.isDisabled(this.editor)}
+				?disabled=${this.api?.isDisabled(this.editor)}
 				@click=${() => this.api?.execute(this.editor)}>
 				${when(
 					this.manifest?.meta.icon,
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-color-picker-button.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-color-picker-button.element.ts
index 07b173accc1f..dc5d10126f7f 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-color-picker-button.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-color-picker-button.element.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarButtonElement } from '../../components/toolbar/tiptap-toolbar-button.element.js';
+import { UmbTiptapToolbarButtonElement } from './tiptap-toolbar-button.element.js';
 import { css, customElement, html, state, when } from '@umbraco-cms/backoffice/external/lit';
 import type { UUIColorPickerChangeEvent } from '@umbraco-cms/backoffice/external/uui';
 
@@ -14,6 +14,7 @@ export class UmbTiptapToolbarColorPickerButtonElement extends UmbTiptapToolbarBu
 
 	override render() {
 		const label = this.localize.string(this.manifest?.meta.label);
+		const disabled = this.api?.isDisabled(this.editor);
 		return html`
 			<uui-button-group>
 				<uui-button
@@ -21,7 +22,7 @@ export class UmbTiptapToolbarColorPickerButtonElement extends UmbTiptapToolbarBu
 					label=${label}
 					popovertarget=${!this._selectedColor ? 'color-picker-popover' : ''}
 					title=${label}
-					?disabled=${this.api && this.editor && this.api.isDisabled(this.editor)}
+					?disabled=${disabled}
 					@click=${() => this.api?.execute(this.editor, this._selectedColor)}>
 					<div>
 						${when(
@@ -32,7 +33,7 @@ export class UmbTiptapToolbarColorPickerButtonElement extends UmbTiptapToolbarBu
 						<div id="color-selected" style="background-color:${this._selectedColor ?? '#000'};"></div>
 					</div>
 				</uui-button>
-				<uui-button compact popovertarget="color-picker-popover" label="Open color picker">
+				<uui-button compact popovertarget="color-picker-popover" label="Open color picker" ?disabled=${disabled}>
 					<uui-symbol-expand open></uui-symbol-expand>
 				</uui-button>
 				<uui-popover-container id="color-picker-popover" placement="bottom-end">
@@ -67,6 +68,12 @@ export class UmbTiptapToolbarColorPickerButtonElement extends UmbTiptapToolbarBu
 			#color-selected {
 				height: var(--uui-size-1);
 			}
+
+			uui-button[disabled] {
+				#color-selected {
+					opacity: 0.3;
+				}
+			}
 		`,
 	];
 }
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-menu.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-menu.element.ts
index 2259de99268c..17f55d6c2fd1 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-menu.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar-menu.element.ts
@@ -3,13 +3,13 @@ import type {
 	MetaTiptapToolbarMenuItem,
 	UmbTiptapToolbarElementApi,
 } from '../../extensions/index.js';
-import type { UmbCascadingMenuItem } from '../../components/cascading-menu-popover/cascading-menu-popover.element.js';
+import type { UmbCascadingMenuItem } from '../cascading-menu-popover/cascading-menu-popover.element.js';
 import { css, customElement, html, state, when } from '@umbraco-cms/backoffice/external/lit';
 import { UmbLitElement } from '@umbraco-cms/backoffice/lit-element';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 import type { ManifestMenu } from '@umbraco-cms/backoffice/menu';
 
-import '../../components/cascading-menu-popover/cascading-menu-popover.element.js';
+import '../cascading-menu-popover/cascading-menu-popover.element.js';
 
 @customElement('umb-tiptap-toolbar-menu')
 export class UmbTiptapToolbarMenuElement extends UmbLitElement {
@@ -118,6 +118,7 @@ export class UmbTiptapToolbarMenuElement extends UmbLitElement {
 
 	override render() {
 		const label = this.localize.string(this.manifest?.meta.label);
+		const disabled = this.api?.isDisabled(this.editor);
 		return html`
 			${when(
 				this.manifest?.meta.look === 'icon',
@@ -127,7 +128,8 @@ export class UmbTiptapToolbarMenuElement extends UmbLitElement {
 						label=${label}
 						look=${this.isActive ? 'outline' : 'default'}
 						title=${label}
-						popovertarget="popover-menu">
+						popovertarget="popover-menu"
+						?disabled=${disabled}>
 						${when(
 							this.manifest?.meta.icon,
 							(icon) => html`<umb-icon name=${icon}></umb-icon>`,
@@ -137,7 +139,12 @@ export class UmbTiptapToolbarMenuElement extends UmbLitElement {
 					</uui-button>
 				`,
 				() => html`
-					<uui-button compact label=${label} look=${this.isActive ? 'outline' : 'default'} popovertarget="popover-menu">
+					<uui-button
+						compact
+						label=${label}
+						look=${this.isActive ? 'outline' : 'default'}
+						popovertarget="popover-menu"
+						?disabled=${disabled}>
 						<span>${label}</span>
 						<uui-symbol-expand slot="extra" open></uui-symbol-expand>
 					</uui-button>
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/tiptap-toolbar.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar.element.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/tiptap-toolbar.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar.element.ts
index 3ac467ad43c8..50e548eec36b 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/input-tiptap/tiptap-toolbar.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/tiptap-toolbar.element.ts
@@ -71,7 +71,7 @@ export class UmbTiptapToolbarElement extends UmbLitElement {
 			},
 			undefined,
 			undefined,
-			() => import('../toolbar/default-tiptap-toolbar-api.js'),
+			() => import('../../extensions/default-tiptap-toolbar-api.js'),
 		);
 
 		this.#extensionsController.apiProperties = { configuration: this.configuration };
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/constants.ts
index a7968c06e642..ab54c9600f75 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/constants.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/constants.ts
@@ -1,5 +1,3 @@
 export * from './contexts/constants.js';
-export * from './components/anchor-modal/constants.js';
-export * from './components/character-map/constants.js';
-export * from './extensions/table/components/constants.js';
-export * from './property-editors/tiptap/constants.js';
+export * from './extensions/constants.js';
+export * from './property-editors/constants.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/anchor.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/anchor.tiptap-api.ts
new file mode 100644
index 000000000000..af01b7e8657e
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/anchor.tiptap-api.ts
@@ -0,0 +1,23 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { css } from '@umbraco-cms/backoffice/external/lit';
+import { Anchor } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapAnchorExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
+	getTiptapExtensions = () => [Anchor];
+
+	override getStyles = () => css`
+		span[data-umb-anchor] {
+			&.ProseMirror-selectednode {
+				border-radius: var(--uui-border-radius);
+				outline: 2px solid var(--uui-color-selected);
+			}
+
+			uui-icon {
+				height: 1rem;
+				width: 1rem;
+				vertical-align: text-bottom;
+			}
+		}
+	`;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/anchor.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/anchor.tiptap-toolbar-api.ts
similarity index 85%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/anchor.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/anchor.tiptap-toolbar-api.ts
index 234df7ae8ab9..29635fd23132 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/anchor.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/anchor.tiptap-toolbar-api.ts
@@ -1,5 +1,5 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
-import { UMB_TIPTAP_ANCHOR_MODAL } from '../../components/anchor-modal/index.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
+import { UMB_TIPTAP_ANCHOR_MODAL } from './modals/index.js';
 import { Anchor } from '@umbraco-cms/backoffice/external/tiptap';
 import { UMB_MODAL_MANAGER_CONTEXT } from '@umbraco-cms/backoffice/modal';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/constants.ts
new file mode 100644
index 000000000000..ea358318ca28
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/constants.ts
@@ -0,0 +1 @@
+export * from './modals/constants.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/index.ts
new file mode 100644
index 000000000000..9e897c4aa454
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/index.ts
@@ -0,0 +1 @@
+export * from './modals/index.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/manifests.ts
new file mode 100644
index 000000000000..2ef13ee73557
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/manifests.ts
@@ -0,0 +1,34 @@
+import { UMB_TIPTAP_ANCHOR_MODAL_ALIAS } from './modals/constants.js';
+
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Anchor',
+		name: 'Anchor Tiptap Extension',
+		api: () => import('./anchor.tiptap-api.js'),
+		meta: {
+			icon: 'icon-anchor',
+			label: '#tiptap_anchor',
+			group: '#tiptap_extGroup_interactive',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Anchor',
+		name: 'Anchor Tiptap Toolbar Extension',
+		api: () => import('./anchor.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Anchor'],
+		meta: {
+			alias: 'anchor',
+			icon: 'icon-anchor',
+			label: '#tiptap_anchor',
+		},
+	},
+	{
+		type: 'modal',
+		alias: UMB_TIPTAP_ANCHOR_MODAL_ALIAS,
+		name: 'Tiptap Anchor Modal',
+		element: () => import('./modals/anchor-modal.element.js'),
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/anchor-modal.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/anchor-modal.element.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/anchor-modal.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/anchor-modal.element.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/anchor-modal.token.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/anchor-modal.token.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/anchor-modal.token.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/anchor-modal.token.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/constants.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/constants.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/constants.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/index.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/anchor-modal/index.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/anchor/modals/index.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tipap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tipap-api.ts
index c90957b1715b..04344ca85a08 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tipap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tipap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { distinctUntilChanged } from '@umbraco-cms/backoffice/external/rxjs';
 import { Node } from '@umbraco-cms/backoffice/external/tiptap';
 import { UMB_BLOCK_RTE_DATA_CONTENT_KEY } from '@umbraco-cms/backoffice/rte';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tiptap-toolbar-api.ts
index 047054cc61a4..822f52a9b984 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/block/block.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import { UMB_BLOCK_RTE_MANAGER_CONTEXT, UMB_BLOCK_RTE_ENTRIES_CONTEXT } from '@umbraco-cms/backoffice/block-rte';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 import type { UmbBlockTypeBaseModel } from '@umbraco-cms/backoffice/block-type';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/blockquote.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/blockquote.tiptap-api.ts
new file mode 100644
index 000000000000..4f8875b256ab
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/blockquote.tiptap-api.ts
@@ -0,0 +1,15 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { css } from '@umbraco-cms/backoffice/external/lit';
+import { Blockquote } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapBlockquoteExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Blockquote];
+
+	override getStyles = () => css`
+		blockquote {
+			border-left: var(--uui-size-1) solid var(--uui-color-border);
+			margin-left: 0;
+			padding-left: var(--uui-size-space-4);
+		}
+	`;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/blockquote.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/blockquote.tiptap-toolbar-api.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/blockquote.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/blockquote.tiptap-toolbar-api.ts
index efd704be6048..d1ad325bec48 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/blockquote.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/blockquote.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarBlockquoteExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/manifests.ts
new file mode 100644
index 000000000000..9938dd4263b1
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/blockquote/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Blockquote',
+		name: 'Blockquote Tiptap Extension',
+		api: () => import('./blockquote.tiptap-api.js'),
+		meta: {
+			icon: 'icon-blockquote',
+			label: 'Blockquote',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Blockquote',
+		name: 'Blockquote Tiptap Toolbar Extension',
+		api: () => import('./blockquote.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Blockquote'],
+		meta: {
+			alias: 'blockquote',
+			icon: 'icon-blockquote',
+			label: 'Blockquote',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/bold.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/bold.tiptap-api.ts
new file mode 100644
index 000000000000..728eea4327e5
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/bold.tiptap-api.ts
@@ -0,0 +1,6 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Bold } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapBoldExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Bold];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/bold.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/bold.tiptap-toolbar-api.ts
similarity index 74%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/bold.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/bold.tiptap-toolbar-api.ts
index 8206a62dc486..347eef751c2e 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/bold.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/bold.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarBoldExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/manifests.ts
new file mode 100644
index 000000000000..a435430ed97a
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bold/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Bold',
+		name: 'Bold Tiptap Extension',
+		api: () => import('./bold.tiptap-api.js'),
+		meta: {
+			icon: 'icon-bold',
+			label: 'Bold',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Bold',
+		name: 'Bold Tiptap Toolbar Extension',
+		api: () => import('./bold.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Bold'],
+		meta: {
+			alias: 'bold',
+			icon: 'icon-bold',
+			label: '#buttons_bold',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/bullet-list.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/bullet-list.tiptap-api.ts
new file mode 100644
index 000000000000..48a6c6b648f2
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/bullet-list.tiptap-api.ts
@@ -0,0 +1,16 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { css } from '@umbraco-cms/backoffice/external/lit';
+import { BulletList, ListItem } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapBulletListExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [ListItem, BulletList];
+
+	override getStyles = () => css`
+		li {
+			> p {
+				margin: 0;
+				padding: 0;
+			}
+		}
+	`;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/bullet-list.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/bullet-list.tiptap-toolbar-api.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/bullet-list.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/bullet-list.tiptap-toolbar-api.ts
index 79fb5d338fd8..c22320cadb86 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/bullet-list.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/bullet-list.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarBulletListExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/manifests.ts
new file mode 100644
index 000000000000..58fdceb9c056
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/bullet-list/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.BulletList',
+		name: 'Bullet List Tiptap Extension',
+		api: () => import('./bullet-list.tiptap-api.js'),
+		meta: {
+			icon: 'icon-bulleted-list',
+			label: 'Bullet List',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.BulletList',
+		name: 'Bullet List Tiptap Toolbar Extension',
+		api: () => import('./bullet-list.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.BulletList'],
+		meta: {
+			alias: 'bulletList',
+			icon: 'icon-bulleted-list',
+			label: '#buttons_listBullet',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/character-map.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/character-map.tiptap-toolbar-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/character-map.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/character-map.tiptap-toolbar-api.ts
index 784a45e242de..ad9167997661 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/character-map.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/character-map.tiptap-toolbar-api.ts
@@ -1,5 +1,5 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
-import { UMB_TIPTAP_CHARACTER_MAP_MODAL } from '../../components/character-map/index.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
+import { UMB_TIPTAP_CHARACTER_MAP_MODAL } from './modals/index.js';
 import { UMB_MODAL_MANAGER_CONTEXT } from '@umbraco-cms/backoffice/modal';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/constants.ts
new file mode 100644
index 000000000000..ea358318ca28
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/constants.ts
@@ -0,0 +1 @@
+export * from './modals/constants.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/index.ts
new file mode 100644
index 000000000000..9e897c4aa454
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/index.ts
@@ -0,0 +1 @@
+export * from './modals/index.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/manifests.ts
new file mode 100644
index 000000000000..cdc8117bd0f9
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/manifests.ts
@@ -0,0 +1,22 @@
+import { UMB_TIPTAP_CHARACTER_MAP_MODAL_ALIAS } from './constants.js';
+
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.CharacterMap',
+		name: 'Character Map Tiptap Toolbar Extension',
+		api: () => import('./character-map.tiptap-toolbar-api.js'),
+		meta: {
+			alias: 'umbCharacterMap',
+			icon: 'icon-omega',
+			label: '#tiptap_charmap',
+		},
+	},
+	{
+		type: 'modal',
+		alias: UMB_TIPTAP_CHARACTER_MAP_MODAL_ALIAS,
+		name: 'Character Map Modal',
+		element: () => import('./modals/character-map-modal.element.js'),
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/character-map-modal.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/character-map-modal.element.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/character-map-modal.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/character-map-modal.element.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/character-map-modal.token.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/character-map-modal.token.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/character-map-modal.token.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/character-map-modal.token.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/constants.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/constants.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/constants.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/index.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/character-map/index.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/character-map/modals/index.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/clear-formatting.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/clear-formatting/clear-formatting.tiptap-toolbar-api.ts
similarity index 78%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/clear-formatting.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/clear-formatting/clear-formatting.tiptap-toolbar-api.ts
index 4f0342731fa7..100ed185cbf4 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/clear-formatting.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/clear-formatting/clear-formatting.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarClearFormattingExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/clear-formatting/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/clear-formatting/manifests.ts
new file mode 100644
index 000000000000..5516bef1fb66
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/clear-formatting/manifests.ts
@@ -0,0 +1,14 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.ClearFormatting',
+		name: 'Clear Formatting Tiptap Toolbar Extension',
+		api: () => import('./clear-formatting.tiptap-toolbar-api.js'),
+		meta: {
+			alias: 'clear-formatting',
+			icon: 'icon-clear-formatting',
+			label: 'Clear Formatting',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/code-block.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/code-block.tiptap-api.ts
new file mode 100644
index 000000000000..b3a4228ecbcd
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/code-block.tiptap-api.ts
@@ -0,0 +1,30 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { css } from '@umbraco-cms/backoffice/external/lit';
+import { Code, CodeBlock } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapCodeBlockExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Code, CodeBlock];
+
+	override getStyles = () => css`
+		pre {
+			background-color: var(--uui-color-surface-alt);
+			padding: var(--uui-size-space-2) var(--uui-size-space-4);
+			border-radius: calc(var(--uui-border-radius) * 2);
+			overflow-x: auto;
+		}
+
+		code:not(pre > code) {
+			background-color: var(--uui-color-surface-alt);
+			padding: var(--uui-size-space-1) var(--uui-size-space-2);
+			border-radius: calc(var(--uui-border-radius) * 2);
+		}
+
+		code {
+			font-family: 'Roboto Mono', monospace;
+			background: none;
+			color: inherit;
+			font-size: 0.8rem;
+			padding: 0;
+		}
+	`;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/code-block.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/code-block.tiptap-toolbar-api.ts
similarity index 78%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/code-block.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/code-block.tiptap-toolbar-api.ts
index f1c8930516ed..496148f69b81 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/code-block.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/code-block.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarCodeBlockExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/manifests.ts
new file mode 100644
index 000000000000..0d866a5307ce
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/code-block/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.CodeBlock',
+		name: 'Code Block Tiptap Extension',
+		api: () => import('./code-block.tiptap-api.js'),
+		meta: {
+			icon: 'icon-code',
+			label: 'Code Block',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.CodeBlock',
+		name: 'Code Block Tiptap Toolbar Extension',
+		api: () => import('./code-block.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.CodeBlock'],
+		meta: {
+			alias: 'codeBlock',
+			icon: 'icon-code',
+			label: 'Code Block',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/constants.ts
new file mode 100644
index 000000000000..b1301a095684
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/constants.ts
@@ -0,0 +1,3 @@
+export * from './anchor/modals/constants.js';
+export * from './character-map/constants.js';
+export * from './table/constants.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/manifests.ts
new file mode 100644
index 000000000000..dafe43c8e7db
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/manifests.ts
@@ -0,0 +1,15 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.RichTextEssentials',
+		name: 'Rich Text Essentials Tiptap Extension',
+		api: () => import('./rich-text-essentials.tiptap-api.js'),
+		weight: 1000,
+		meta: {
+			icon: 'icon-browser-window',
+			label: 'Rich Text Essentials',
+			group: '#tiptap_extGroup_formatting',
+			description: 'This is a core extension, it is always enabled by default.',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/rich-text-essentials.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/rich-text-essentials.tiptap-api.ts
index 9a3e2fb22baa..c67a42801e61 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/rich-text-essentials.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/rich-text-essentials.tiptap-api.ts
@@ -1,105 +1,14 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
-import { css } from '@umbraco-cms/backoffice/external/lit';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import {
-	Anchor,
-	Div,
-	HtmlGlobalAttributes,
-	Span,
-	StarterKit,
-	TrailingNode,
+	Document,
+	Dropcursor,
+	Gapcursor,
+	HardBreak,
+	History,
+	Paragraph,
+	Text,
 } from '@umbraco-cms/backoffice/external/tiptap';
 
-export class UmbTiptapRichTextEssentialsExtensionApi extends UmbTiptapExtensionApiBase {
-	getTiptapExtensions = () => [
-		StarterKit,
-		Anchor,
-		Div,
-		Span,
-		HtmlGlobalAttributes.configure({
-			types: [
-				'bold',
-				'blockquote',
-				'bulletList',
-				'codeBlock',
-				'div',
-				'figcaption',
-				'figure',
-				'heading',
-				'horizontalRule',
-				'italic',
-				'image',
-				'link',
-				'orderedList',
-				'paragraph',
-				'span',
-				'strike',
-				'subscript',
-				'superscript',
-				'table',
-				'tableHeader',
-				'tableRow',
-				'tableCell',
-				'underline',
-				'umbLink',
-			],
-		}),
-		TrailingNode,
-	];
-
-	override getStyles = () => css`
-		pre {
-			background-color: var(--uui-color-surface-alt);
-			padding: var(--uui-size-space-2) var(--uui-size-space-4);
-			border-radius: calc(var(--uui-border-radius) * 2);
-			overflow-x: auto;
-		}
-
-		code:not(pre > code) {
-			background-color: var(--uui-color-surface-alt);
-			padding: var(--uui-size-space-1) var(--uui-size-space-2);
-			border-radius: calc(var(--uui-border-radius) * 2);
-		}
-
-		code {
-			font-family: 'Roboto Mono', monospace;
-			background: none;
-			color: inherit;
-			font-size: 0.8rem;
-			padding: 0;
-		}
-
-		h1,
-		h2,
-		h3,
-		h4,
-		h5,
-		h6 {
-			margin-top: 0;
-			margin-bottom: 0.5em;
-		}
-
-		li {
-			> p {
-				margin: 0;
-				padding: 0;
-			}
-		}
-
-		span[data-umb-anchor] {
-			&.ProseMirror-selectednode {
-				border-radius: var(--uui-border-radius);
-				outline: 2px solid var(--uui-color-selected);
-			}
-
-			uui-icon {
-				height: 1rem;
-				width: 1rem;
-				vertical-align: text-bottom;
-			}
-		}
-	`;
+export default class UmbTiptapRichTextEssentialsExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Document, Dropcursor, Gapcursor, HardBreak, History, Paragraph, Text];
 }
-
-export default UmbTiptapRichTextEssentialsExtensionApi;
-
-export { UmbTiptapRichTextEssentialsExtensionApi as api };
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/default-tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/default-tiptap-toolbar-api.ts
similarity index 60%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/default-tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/default-tiptap-toolbar-api.ts
index 9d845ccb92b4..55da798d2aae 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/default-tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/default-tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../../extensions/base.js';
+import { UmbTiptapToolbarElementApiBase } from './tiptap-toolbar-element-api-base.js';
 
 export default class UmbTiptapToolbarDefaultExtensionApi extends UmbTiptapToolbarElementApiBase {
 	public override execute() {}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/element-path.tiptap-statusbar-element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/element-path/element-path.tiptap-statusbar-element.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/element-path.tiptap-statusbar-element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/element-path/element-path.tiptap-statusbar-element.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/element-path/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/element-path/manifests.ts
new file mode 100644
index 000000000000..368caf4fe7dc
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/element-path/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapStatusbarExtension',
+		alias: 'Umb.Tiptap.Statusbar.ElementPath',
+		name: 'Element Path Tiptap Statusbar Extension',
+		element: () => import('./element-path.tiptap-statusbar-element.js'),
+		meta: {
+			alias: 'elementPath',
+			icon: 'icon-map-alt',
+			label: 'Element Path',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/embedded-media.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/embedded-media.tiptap-api.ts
similarity index 84%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/embedded-media.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/embedded-media.tiptap-api.ts
index 8ffdb2abf194..425df096b3c2 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/embedded-media.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/embedded-media.tiptap-api.ts
@@ -1,8 +1,9 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { css } from '@umbraco-cms/backoffice/external/lit';
 import { umbEmbeddedMedia } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapEmbeddedMediaExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
 	getTiptapExtensions = () => [umbEmbeddedMedia.configure({ inline: true })];
 
 	override getStyles = () => css`
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/embedded-media.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/embedded-media.tiptap-toolbar-api.ts
similarity index 92%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/embedded-media.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/embedded-media.tiptap-toolbar-api.ts
index d3a5509ab887..4657e783da75 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/embedded-media.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/embedded-media.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import { umbEmbeddedMedia } from '@umbraco-cms/backoffice/external/tiptap';
 import { UMB_EMBEDDED_MEDIA_MODAL } from '@umbraco-cms/backoffice/embedded-media';
 import { umbOpenModal } from '@umbraco-cms/backoffice/modal';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/manifests.ts
new file mode 100644
index 000000000000..d299978d5502
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/embedded-media/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Embed',
+		name: 'Embedded Media Tiptap Extension',
+		api: () => import('./embedded-media.tiptap-api.js'),
+		meta: {
+			icon: 'icon-embed',
+			label: '#general_embed',
+			group: '#tiptap_extGroup_media',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.EmbeddedMedia',
+		name: 'Embedded Media Tiptap Toolbar Extension',
+		api: () => import('./embedded-media.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Embed'],
+		meta: {
+			alias: 'umbEmbeddedMedia',
+			icon: 'icon-embed',
+			label: '#general_embed',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/figure.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/figure/figure.tiptap-api.ts
similarity index 60%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/figure.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/figure/figure.tiptap-api.ts
index 0b879bb89ee2..eb1995474c2b 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/figure.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/figure/figure.tiptap-api.ts
@@ -1,6 +1,7 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { Figure, Figcaption } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapFigureExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
 	getTiptapExtensions = () => [Figcaption, Figure];
 }
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/figure/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/figure/manifests.ts
new file mode 100644
index 000000000000..ef5157228652
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/figure/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Figure',
+		name: 'Figure Tiptap Extension',
+		api: () => import('./figure.tiptap-api.js'),
+		meta: {
+			icon: 'icon-frame',
+			label: 'Figure',
+			group: '#tiptap_extGroup_media',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/font-family.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-family/font-family.tiptap-toolbar-api.ts
similarity index 87%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/font-family.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-family/font-family.tiptap-toolbar-api.ts
index 4b4c92e03f81..fa5e1a7a9a24 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/font-family.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-family/font-family.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { MetaTiptapToolbarMenuItem } from '../types.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-family/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-family/manifests.ts
new file mode 100644
index 000000000000..9adf88c4488e
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-family/manifests.ts
@@ -0,0 +1,35 @@
+const UMB_MENU_TIPTAP_FONT_FAMILY_ALIAS = 'Umb.Menu.Tiptap.FontFamily';
+
+const menu: Array<UmbExtensionManifest> = [
+	{
+		type: 'menu',
+		alias: UMB_MENU_TIPTAP_FONT_FAMILY_ALIAS,
+		name: 'Tiptap Font Family Menu',
+	},
+];
+
+const toolbarExtensions: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'menu',
+		alias: 'Umb.Tiptap.Toolbar.FontFamily',
+		name: 'Font Family Tiptap Toolbar Extension',
+		api: () => import('./font-family.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.HtmlAttributeStyle', 'Umb.Tiptap.HtmlTagSpan'],
+		items: [
+			{ label: 'Sans serif', appearance: { style: 'font-family: sans-serif;' }, data: 'sans-serif' },
+			{ label: 'Serif', appearance: { style: 'font-family: serif;' }, data: 'serif' },
+			{ label: 'Monospace', appearance: { style: 'font-family: monospace;' }, data: 'monospace' },
+			{ label: 'Cursive', appearance: { style: 'font-family: cursive;' }, data: 'cursive' },
+			{ label: 'Fantasy', appearance: { style: 'font-family: fantasy;' }, data: 'fantasy' },
+		],
+		menu: UMB_MENU_TIPTAP_FONT_FAMILY_ALIAS,
+		meta: {
+			alias: 'umbFontFamily',
+			icon: 'icon-ruler-alt',
+			label: 'Font family',
+		},
+	},
+];
+
+export const manifests: Array<UmbExtensionManifest> = [...menu, ...toolbarExtensions];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/font-size.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-size/font-size.tiptap-toolbar-api.ts
similarity index 87%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/font-size.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-size/font-size.tiptap-toolbar-api.ts
index d2ce175dee75..29ad66e40d5c 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/font-size.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-size/font-size.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { MetaTiptapToolbarMenuItem } from '../types.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-size/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-size/manifests.ts
new file mode 100644
index 000000000000..d4c3e7b0b73f
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/font-size/manifests.ts
@@ -0,0 +1,39 @@
+const UMB_MENU_TIPTAP_FONT_SIZE_ALIAS = 'Umb.Menu.Tiptap.FontSize';
+
+const menu: Array<UmbExtensionManifest> = [
+	{
+		type: 'menu',
+		alias: UMB_MENU_TIPTAP_FONT_SIZE_ALIAS,
+		name: 'Tiptap Font Size Menu',
+	},
+];
+
+const toolbarExtensions: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'menu',
+		alias: 'Umb.Tiptap.Toolbar.FontSize',
+		name: 'Font Size Tiptap Toolbar Extension',
+		api: () => import('./font-size.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.HtmlAttributeStyle', 'Umb.Tiptap.HtmlTagSpan'],
+		items: [
+			{ label: '8pt', data: '8pt' },
+			{ label: '10pt', data: '10pt' },
+			{ label: '12pt', data: '12pt' },
+			{ label: '14pt', data: '14pt' },
+			{ label: '16pt', data: '16pt' },
+			{ label: '18pt', data: '18pt' },
+			{ label: '24pt', data: '24pt' },
+			{ label: '26pt', data: '26pt' },
+			{ label: '48pt', data: '48pt' },
+		],
+		menu: UMB_MENU_TIPTAP_FONT_SIZE_ALIAS,
+		meta: {
+			alias: 'umbFontSize',
+			icon: 'icon-ruler',
+			label: 'Font size',
+		},
+	},
+];
+
+export const manifests: Array<UmbExtensionManifest> = [...menu, ...toolbarExtensions];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading.tiptap-api.ts
new file mode 100644
index 000000000000..d733e8323443
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading.tiptap-api.ts
@@ -0,0 +1,19 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { css } from '@umbraco-cms/backoffice/external/lit';
+import { Heading } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapHeadingExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Heading];
+
+	override getStyles = () => css`
+		h1,
+		h2,
+		h3,
+		h4,
+		h5,
+		h6 {
+			margin-top: 0;
+			margin-bottom: 0.5em;
+		}
+	`;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading1.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading1.tiptap-toolbar-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading1.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading1.tiptap-toolbar-api.ts
index a9fd015ba908..3f1993557c09 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading1.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading1.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarHeading1ExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading2.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading2.tiptap-toolbar-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading2.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading2.tiptap-toolbar-api.ts
index 1274bd0e263d..345824512abc 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading2.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading2.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarHeading2ExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading3.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading3.tiptap-toolbar-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading3.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading3.tiptap-toolbar-api.ts
index cb40b09cded3..3706b6c8bcf4 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/heading3.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/heading3.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarHeading3ExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/manifests.ts
new file mode 100644
index 000000000000..8655614e0350
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/heading/manifests.ts
@@ -0,0 +1,52 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Heading',
+		name: 'Headings Tiptap Extension',
+		api: () => import('./heading.tiptap-api.js'),
+		meta: {
+			icon: 'icon-heading-1',
+			label: 'Headings',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Heading1',
+		name: 'Heading 1 Tiptap Toolbar Extension',
+		api: () => import('./heading1.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Heading'],
+		meta: {
+			alias: 'heading1',
+			icon: 'icon-heading-1',
+			label: 'Heading 1',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Heading2',
+		name: 'Heading 2 Tiptap Toolbar Extension',
+		api: () => import('./heading2.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Heading'],
+		meta: {
+			alias: 'heading2',
+			icon: 'icon-heading-2',
+			label: 'Heading 2',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Heading3',
+		name: 'Heading 3 Tiptap Toolbar Extension',
+		api: () => import('./heading3.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Heading'],
+		meta: {
+			alias: 'heading3',
+			icon: 'icon-heading-3',
+			label: 'Heading 3',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/horizontal-rule.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/horizontal-rule.tiptap-api.ts
new file mode 100644
index 000000000000..b07d0ca74de0
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/horizontal-rule.tiptap-api.ts
@@ -0,0 +1,6 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { HorizontalRule } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapHorizontalRuleExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [HorizontalRule];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/horizontal-rule.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/horizontal-rule.tiptap-toolbar-api.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/horizontal-rule.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/horizontal-rule.tiptap-toolbar-api.ts
index 2ac3ddd0abf5..2305c5d8dcaf 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/horizontal-rule.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/horizontal-rule.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarHorizontalRuleExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/manifests.ts
new file mode 100644
index 000000000000..47523bb921b5
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/horizontal-rule/manifests.ts
@@ -0,0 +1,25 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HorizontalRule',
+		name: 'Horizontal Rule Tiptap Extension',
+		api: () => import('./horizontal-rule.tiptap-api.js'),
+		meta: {
+			icon: 'icon-horizontal-rule',
+			label: 'Horizontal Rule',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.HorizontalRule',
+		name: 'Horizontal Rule Tiptap Toolbar Extension',
+		api: () => import('./horizontal-rule.tiptap-toolbar-api.js'),
+		meta: {
+			alias: 'horizontalRule',
+			icon: 'icon-horizontal-rule',
+			label: 'Horizontal Rule',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-api.ts
new file mode 100644
index 000000000000..a44680a341f1
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/html-attr-class.tiptap-api.ts
@@ -0,0 +1,95 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Extension } from '@umbraco-cms/backoffice/external/tiptap';
+import type { Attributes } from '@umbraco-cms/backoffice/external/tiptap';
+
+declare module '@tiptap/core' {
+	interface Commands<ReturnType> {
+		htmlClassAttribute: {
+			setClassName: (className?: string, type?: string) => ReturnType;
+			toggleClassName: (className?: string, type?: string) => ReturnType;
+			unsetClassName: (type?: string) => ReturnType;
+		};
+	}
+}
+
+interface HtmlClassAttributeOptions {
+	types: Array<string>;
+}
+
+const HtmlClassAttribute = Extension.create<HtmlClassAttributeOptions>({
+	name: 'htmlClassAttribute',
+
+	addOptions() {
+		return { types: [] };
+	},
+
+	addGlobalAttributes() {
+		return [
+			{
+				types: this.options.types,
+				attributes: { class: {} } as Attributes,
+			},
+		];
+	},
+
+	addCommands() {
+		return {
+			setClassName:
+				(className, type) =>
+				({ commands }) => {
+					if (!className) return false;
+					const types = type ? [type] : this.options.types;
+					return types
+						.map((type) => commands.updateAttributes(type, { class: className }))
+						.every((response) => response);
+				},
+			toggleClassName:
+				(className, type) =>
+				({ 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);
+				},
+			unsetClassName:
+				(type) =>
+				({ commands }) => {
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.resetAttributes(type, 'class')).every((response) => response);
+				},
+		};
+	},
+});
+
+export default class UmbTiptapHtmlAttributeClassExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [
+		HtmlClassAttribute.configure({
+			types: [
+				'bold',
+				'blockquote',
+				'bulletList',
+				'codeBlock',
+				'div',
+				'figcaption',
+				'figure',
+				'heading',
+				'horizontalRule',
+				'italic',
+				'image',
+				'link',
+				'orderedList',
+				'paragraph',
+				'span',
+				'strike',
+				'subscript',
+				'superscript',
+				'table',
+				'tableHeader',
+				'tableRow',
+				'tableCell',
+				'underline',
+				'umbLink',
+			],
+		}),
+	];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/manifests.ts
new file mode 100644
index 000000000000..01badb125f75
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-class/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HtmlAttributeClass',
+		name: 'Class HTML Attribute Tiptap Extension',
+		api: () => import('./html-attr-class.tiptap-api.js'),
+		meta: {
+			icon: 'icon-barcode',
+			label: '`class` attributes',
+			group: '#tiptap_extGroup_html',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-dataset/html-attr-dataset.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-dataset/html-attr-dataset.tiptap-api.ts
new file mode 100644
index 000000000000..91bba989cb9d
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-dataset/html-attr-dataset.tiptap-api.ts
@@ -0,0 +1,115 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Extension } from '@umbraco-cms/backoffice/external/tiptap';
+import type { Attributes } from '@umbraco-cms/backoffice/external/tiptap';
+
+declare module '@tiptap/core' {
+	interface Commands<ReturnType> {
+		htmlDatasetAttributes: {
+			setId: (id?: string, type?: string) => ReturnType;
+			toggleId: (id?: string, type?: string) => ReturnType;
+			unsetId: (type?: string) => ReturnType;
+		};
+	}
+}
+
+/**
+ * Converts camelCase to kebab-case.
+ * @param {string} str - The string to convert.
+ * @returns {string} The converted string.
+ */
+function camelCaseToKebabCase(str: string): string {
+	return str.replace(/[A-Z]+(?![a-z])|[A-Z]/g, ($, ofs) => (ofs ? '-' : '') + $.toLowerCase());
+}
+
+interface HtmlDatasetAttributesOptions {
+	types: Array<string>;
+}
+
+const HtmlDatasetAttributes = Extension.create<HtmlDatasetAttributesOptions>({
+	name: 'htmlDatasetAttributes',
+
+	addOptions() {
+		return { types: [] };
+	},
+
+	addGlobalAttributes() {
+		return [
+			{
+				types: this.options.types,
+				attributes: {
+					dataset: {
+						parseHTML: (element) => element.dataset,
+						renderHTML: (attributes) => {
+							const keys = attributes.dataset ? Object.keys(attributes.dataset) : [];
+							if (!keys.length) return {};
+							const dataAtrrs: Record<string, string> = {};
+							keys.forEach((key) => {
+								dataAtrrs['data-' + camelCaseToKebabCase(key)] = attributes.dataset[key];
+							});
+							return dataAtrrs;
+						},
+					},
+				} as Attributes,
+			},
+		];
+	},
+
+	addCommands() {
+		return {
+			setId:
+				(id, type) =>
+				({ commands }) => {
+					if (!id) return false;
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.updateAttributes(type, { id })).every((response) => response);
+				},
+			toggleId:
+				(id, type) =>
+				({ commands, editor }) => {
+					if (!id) return false;
+					const types = type ? [type] : this.options.types;
+					const existing = types.map((type) => editor.getAttributes(type)?.id as string).filter((x) => x);
+					return existing.length ? commands.unsetId(type) : commands.setId(id, type);
+				},
+			unsetId:
+				(type) =>
+				({ commands }) => {
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.resetAttributes(type, 'id')).every((response) => response);
+				},
+		};
+	},
+});
+
+export default class UmbTiptapHtmlAttributeDatasetExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [
+		HtmlDatasetAttributes.configure({
+			types: [
+				'bold',
+				'blockquote',
+				'bulletList',
+				'codeBlock',
+				'div',
+				'figcaption',
+				'figure',
+				'heading',
+				'horizontalRule',
+				'italic',
+				'image',
+				'link',
+				'orderedList',
+				'paragraph',
+				'span',
+				'strike',
+				'subscript',
+				'superscript',
+				'table',
+				'tableHeader',
+				'tableRow',
+				'tableCell',
+				'underline',
+				'umbLink',
+			],
+		}),
+	];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-dataset/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-dataset/manifests.ts
new file mode 100644
index 000000000000..44aca270a0ff
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-dataset/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HtmlAttributeDataset',
+		name: 'Dataset HTML Attribute Tiptap Extension',
+		api: () => import('./html-attr-dataset.tiptap-api.js'),
+		meta: {
+			icon: 'icon-binarycode',
+			label: '`data-*` attributes',
+			group: '#tiptap_extGroup_html',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-id/html-attr-id.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-id/html-attr-id.tiptap-api.ts
new file mode 100644
index 000000000000..017d070585c8
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-id/html-attr-id.tiptap-api.ts
@@ -0,0 +1,93 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Extension } from '@umbraco-cms/backoffice/external/tiptap';
+import type { Attributes } from '@umbraco-cms/backoffice/external/tiptap';
+
+declare module '@tiptap/core' {
+	interface Commands<ReturnType> {
+		htmlIdAttribute: {
+			setId: (id?: string, type?: string) => ReturnType;
+			toggleId: (id?: string, type?: string) => ReturnType;
+			unsetId: (type?: string) => ReturnType;
+		};
+	}
+}
+
+interface HtmlIdAttributeOptions {
+	types: Array<string>;
+}
+
+const HtmlIdAttribute = Extension.create<HtmlIdAttributeOptions>({
+	name: 'htmlIdAttribute',
+
+	addOptions() {
+		return { types: [] };
+	},
+
+	addGlobalAttributes() {
+		return [
+			{
+				types: this.options.types,
+				attributes: { id: {} } as Attributes,
+			},
+		];
+	},
+
+	addCommands() {
+		return {
+			setId:
+				(id, type) =>
+				({ commands }) => {
+					if (!id) return false;
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.updateAttributes(type, { id })).every((response) => response);
+				},
+			toggleId:
+				(id, type) =>
+				({ commands, editor }) => {
+					if (!id) return false;
+					const types = type ? [type] : this.options.types;
+					const existing = types.map((type) => editor.getAttributes(type)?.id as string).filter((x) => x);
+					return existing.length ? commands.unsetId(type) : commands.setId(id, type);
+				},
+			unsetId:
+				(type) =>
+				({ commands }) => {
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.resetAttributes(type, 'id')).every((response) => response);
+				},
+		};
+	},
+});
+
+export default class UmbTiptapHtmlAttributeIdExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [
+		HtmlIdAttribute.configure({
+			types: [
+				'bold',
+				'blockquote',
+				'bulletList',
+				'codeBlock',
+				'div',
+				'figcaption',
+				'figure',
+				'heading',
+				'horizontalRule',
+				'italic',
+				'image',
+				'link',
+				'orderedList',
+				'paragraph',
+				'span',
+				'strike',
+				'subscript',
+				'superscript',
+				'table',
+				'tableHeader',
+				'tableRow',
+				'tableCell',
+				'underline',
+				'umbLink',
+			],
+		}),
+	];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-id/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-id/manifests.ts
new file mode 100644
index 000000000000..b77fedc7bf84
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-id/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HtmlAttributeId',
+		name: 'ID HTML Attribute Tiptap Extension',
+		api: () => import('./html-attr-id.tiptap-api.js'),
+		meta: {
+			icon: 'icon-fingerprint',
+			label: '`id` attributes',
+			group: '#tiptap_extGroup_html',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-style/html-attr-style.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-style/html-attr-style.tiptap-api.ts
new file mode 100644
index 000000000000..324c968afe67
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-style/html-attr-style.tiptap-api.ts
@@ -0,0 +1,97 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Extension } from '@umbraco-cms/backoffice/external/tiptap';
+import type { Attributes } from '@umbraco-cms/backoffice/external/tiptap';
+
+declare module '@tiptap/core' {
+	interface Commands<ReturnType> {
+		htmlStyleAttribute: {
+			setStyles: (style?: string, type?: string) => ReturnType;
+			toggleStyles: (style?: string, type?: string) => ReturnType;
+			unsetStyles: (type?: string) => ReturnType;
+		};
+	}
+}
+
+interface HtmlStyleAttributeOptions {
+	types: Array<string>;
+}
+
+const HtmlStyleAttribute = Extension.create<HtmlStyleAttributeOptions>({
+	name: 'htmlStyleAttribute',
+
+	addOptions() {
+		return { types: [] };
+	},
+
+	addGlobalAttributes() {
+		return [
+			{
+				types: this.options.types,
+				attributes: {
+					style: {
+						parseHTML: (element) => (element.style.length ? element.style.cssText : null),
+					},
+				} as Attributes,
+			},
+		];
+	},
+
+	addCommands() {
+		return {
+			setStyles:
+				(style, type) =>
+				({ commands }) => {
+					if (!style) return false;
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.updateAttributes(type, { style })).every((response) => response);
+				},
+			toggleStyles:
+				(style, type) =>
+				({ commands, editor }) => {
+					if (!style) return false;
+					const types = type ? [type] : this.options.types;
+					const existing = types.map((type) => editor.getAttributes(type)?.style as string).filter((x) => x);
+					return existing.length ? commands.unsetStyles(type) : commands.setStyles(style, type);
+				},
+			unsetStyles:
+				(type) =>
+				({ commands }) => {
+					const types = type ? [type] : this.options.types;
+					return types.map((type) => commands.resetAttributes(type, 'style')).every((response) => response);
+				},
+		};
+	},
+});
+
+export default class UmbTiptapHtmlAttributeStyleExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [
+		HtmlStyleAttribute.configure({
+			types: [
+				'bold',
+				'blockquote',
+				'bulletList',
+				'codeBlock',
+				'div',
+				'figcaption',
+				'figure',
+				'heading',
+				'horizontalRule',
+				'italic',
+				'image',
+				'link',
+				'orderedList',
+				'paragraph',
+				'span',
+				'strike',
+				'subscript',
+				'superscript',
+				'table',
+				'tableHeader',
+				'tableRow',
+				'tableCell',
+				'underline',
+				'umbLink',
+			],
+		}),
+	];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-style/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-style/manifests.ts
new file mode 100644
index 000000000000..edc851a0e2fc
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-attr-style/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HtmlAttributeStyle',
+		name: 'Style HTML Attribute Tiptap Extension',
+		api: () => import('./html-attr-style.tiptap-api.js'),
+		meta: {
+			icon: 'icon-palette',
+			label: '`style` attributes',
+			group: '#tiptap_extGroup_html',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-div/html-tag-div.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-div/html-tag-div.tiptap-api.ts
new file mode 100644
index 000000000000..5c6f1cd5fbc0
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-div/html-tag-div.tiptap-api.ts
@@ -0,0 +1,7 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Div } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapHtmlTagDivExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
+	getTiptapExtensions = () => [Div];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-div/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-div/manifests.ts
new file mode 100644
index 000000000000..ac85724183f6
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-div/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HtmlTagDiv',
+		name: 'Div HTML Tag Tiptap Extension',
+		api: () => import('./html-tag-div.tiptap-api.js'),
+		meta: {
+			icon: 'icon-document-html',
+			label: '`<div>` tags',
+			group: '#tiptap_extGroup_html',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-span/html-tag-span.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-span/html-tag-span.tiptap-api.ts
new file mode 100644
index 000000000000..a4c7491dc8a1
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-span/html-tag-span.tiptap-api.ts
@@ -0,0 +1,7 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Span } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapHtmlTagSpanExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
+	getTiptapExtensions = () => [Span];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-span/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-span/manifests.ts
new file mode 100644
index 000000000000..0265382a0076
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/html-tag-span/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.HtmlTagSpan',
+		name: 'Span HTML Tag Tiptap Extension',
+		api: () => import('./html-tag-span.tiptap-api.js'),
+		meta: {
+			icon: 'icon-document-html',
+			label: '`<span>` tags',
+			group: '#tiptap_extGroup_html',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/image.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/image/image.tiptap-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/image.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/image/image.tiptap-api.ts
index 1d7a2da44963..3c09402edc30 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/image.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/image/image.tiptap-api.ts
@@ -1,8 +1,9 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { css } from '@umbraco-cms/backoffice/external/lit';
 import { UmbImage } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapImageExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
 	getTiptapExtensions = () => [UmbImage.configure({ inline: true })];
 
 	override getStyles = () => css`
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/image/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/image/manifests.ts
new file mode 100644
index 000000000000..22ad0583ba74
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/image/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Image',
+		name: 'Image Tiptap Extension',
+		api: () => import('./image.tiptap-api.js'),
+		meta: {
+			icon: 'icon-picture',
+			label: 'Image',
+			group: '#tiptap_extGroup_media',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/index.ts
index 3442599e469a..e67d8949fb83 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/index.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/index.ts
@@ -1,3 +1,7 @@
-export * from './base.js';
+export * from './tiptap-extension-api-base.js';
+export * from './tiptap-toolbar-element-api-base.js';
+export * from './anchor/index.js';
+export * from './character-map/index.js';
 export * from './table/index.js';
+
 export type * from './types.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/italic.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/italic.tiptap-api.ts
new file mode 100644
index 000000000000..49a3077adc8b
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/italic.tiptap-api.ts
@@ -0,0 +1,7 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Italic } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapItalicExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Italic];
+}
+
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/italic.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/italic.tiptap-toolbar-api.ts
similarity index 74%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/italic.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/italic.tiptap-toolbar-api.ts
index 9e329a1c3713..68d1f7620b03 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/italic.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/italic.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarItalicExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/manifests.ts
new file mode 100644
index 000000000000..fe75d0872000
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/italic/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Italic',
+		name: 'Italic Tiptap Extension',
+		api: () => import('./italic.tiptap-api.js'),
+		meta: {
+			icon: 'icon-italic',
+			label: 'Italic',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Italic',
+		name: 'Italic Tiptap Toolbar Extension',
+		api: () => import('./italic.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Italic'],
+		meta: {
+			alias: 'italic',
+			icon: 'icon-italic',
+			label: '#buttons_italic',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/link.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-api.ts
similarity index 62%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/link.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-api.ts
index 47fcb00118fb..300df0ef2f55 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/link.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-api.ts
@@ -1,6 +1,7 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { UmbLink } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapLinkExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
 	getTiptapExtensions = () => [UmbLink.configure({ openOnClick: false })];
 }
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/link.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-toolbar-api.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/link.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-toolbar-api.ts
index a369af6a0f82..9038afedb1fe 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/link.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/link.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import { UmbLink } from '@umbraco-cms/backoffice/external/tiptap';
 import { UMB_LINK_PICKER_MODAL } from '@umbraco-cms/backoffice/multi-url-picker';
 import { umbOpenModal } from '@umbraco-cms/backoffice/modal';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/manifests.ts
new file mode 100644
index 000000000000..b3c1ff40add7
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/manifests.ts
@@ -0,0 +1,40 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Link',
+		name: 'Link Tiptap Extension',
+		api: () => import('./link.tiptap-api.js'),
+		meta: {
+			icon: 'icon-link',
+			label: '#defaultdialogs_urlLinkPicker',
+			group: '#tiptap_extGroup_interactive',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Link',
+		name: 'Link Tiptap Toolbar Extension',
+		api: () => import('./link.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Link'],
+		meta: {
+			alias: 'umbLink',
+			icon: 'icon-link',
+			label: '#defaultdialogs_urlLinkPicker',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Unlink',
+		name: 'Unlink Tiptap Toolbar Extension',
+		api: () => import('./unlink.tiptap-toolbar-api.js'),
+		element: () => import('../../components/toolbar/tiptap-toolbar-button-disabled.element.js'),
+		forExtensions: ['Umb.Tiptap.Link'],
+		meta: {
+			alias: 'unlink',
+			icon: 'icon-unlink',
+			label: 'Unlink',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/unlink.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/unlink.tiptap-toolbar-api.ts
similarity index 82%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/unlink.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/unlink.tiptap-toolbar-api.ts
index 68b6acfc251f..43c8ea90132c 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/unlink.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/link/unlink.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarUnlinkExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/manifests.ts
index 1e96b7751960..d1442a396dec 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/manifests.ts
@@ -1,678 +1,94 @@
-import { manifests as blockExtensions } from './block/manifests.js';
-import { manifests as styleSelectExtensions } from './style-select/manifests.js';
-import { manifests as tableExtensions } from './table/manifests.js';
-import { manifests as statusbarExtensions } from './statusbar/manifests.js';
-import type { ManifestTiptapExtension } from './tiptap.extension.js';
-import type { UmbExtensionManifestKind } from '@umbraco-cms/backoffice/extension-registry';
+import { manifest as buttonKind } from './tiptap-toolbar-button.kind.js';
+import { manifest as colorPickerButton } from './tiptap-toolbar-color-picker-button.kind.js';
+import { manifest as menuButton } from './tiptap-toolbar-menu.kind.js';
+import { manifest as styleMenuKind } from './style-menu/style-menu.kind.js';
+import { manifests as anchor } from './anchor/manifests.js';
+import { manifests as block } from './block/manifests.js';
+import { manifests as blockquote } from './blockquote/manifests.js';
+import { manifests as bold } from './bold/manifests.js';
+import { manifests as bulletList } from './bullet-list/manifests.js';
+import { manifests as characterMap } from './character-map/manifests.js';
+import { manifests as clearFormatting } from './clear-formatting/manifests.js';
+import { manifests as codeBlock } from './code-block/manifests.js';
+import { manifests as core } from './core/manifests.js';
+import { manifests as elementPath } from './element-path/manifests.js';
+import { manifests as embeddedMedia } from './embedded-media/manifests.js';
+import { manifests as figure } from './figure/manifests.js';
+import { manifests as fontFamily } from './font-family/manifests.js';
+import { manifests as fontSize } from './font-size/manifests.js';
+import { manifests as heading } from './heading/manifests.js';
+import { manifests as horizontalRule } from './horizontal-rule/manifests.js';
+import { manifests as htmlAttrClass } from './html-attr-class/manifests.js';
+import { manifests as htmlAttrDataset } from './html-attr-dataset/manifests.js';
+import { manifests as htmlAttrId } from './html-attr-id/manifests.js';
+import { manifests as htmlAttrStyle } from './html-attr-style/manifests.js';
+import { manifests as htmlTagDiv } from './html-tag-div/manifests.js';
+import { manifests as htmlTagSpan } from './html-tag-span/manifests.js';
+import { manifests as image } from './image/manifests.js';
+import { manifests as italic } from './italic/manifests.js';
+import { manifests as link } from './link/manifests.js';
+import { manifests as mediaPicker } from './media-picker/manifests.js';
+import { manifests as mediaUpload } from './media-upload/manifests.js';
+import { manifests as orderedList } from './ordered-list/manifests.js';
+import { manifests as strike } from './strike/manifests.js';
+import { manifests as styleSelect } from './style-select/manifests.js';
+import { manifests as subscript } from './subscript/manifests.js';
+import { manifests as superscript } from './superscript/manifests.js';
+import { manifests as table } from './table/manifests.js';
+import { manifests as textAlign } from './text-align/manifests.js';
+import { manifests as textColor } from './text-color/manifests.js';
+import { manifests as textDirection } from './text-direction/manifests.js';
+import { manifests as textIndent } from './text-indent/manifests.js';
+import { manifests as trailingNode } from './trailing-node/manifests.js';
+import { manifests as underline } from './underline/manifests.js';
+import { manifests as undoRedo } from './undo-redo/manifests.js';
+import { manifests as viewSource } from './view-source/manifests.js';
+import { manifests as wordCount } from './word-count/manifests.js';
 
-const kinds: Array<UmbExtensionManifestKind> = [
-	{
-		type: 'kind',
-		alias: 'Umb.Kind.TiptapToolbar.Button',
-		matchKind: 'button',
-		matchType: 'tiptapToolbarExtension',
-		manifest: {
-			element: () => import('../components/toolbar/tiptap-toolbar-button.element.js'),
-		},
-	},
-	{
-		type: 'kind',
-		alias: 'Umb.Kind.TiptapToolbar.ColorPickerButton',
-		matchKind: 'colorPickerButton',
-		matchType: 'tiptapToolbarExtension',
-		manifest: {
-			element: () => import('../components/toolbar/tiptap-toolbar-color-picker-button.element.js'),
-		},
-	},
-	{
-		type: 'kind',
-		alias: 'Umb.Kind.TiptapToolbar.Menu',
-		matchKind: 'menu',
-		matchType: 'tiptapToolbarExtension',
-		manifest: {
-			element: () => import('../components/toolbar/tiptap-toolbar-menu.element.js'),
-		},
-	},
-	{
-		type: 'kind',
-		alias: 'Umb.Kind.TiptapToolbar.StyleMenu',
-		matchKind: 'styleMenu',
-		matchType: 'tiptapToolbarExtension',
-		manifest: {
-			api: () => import('../components/toolbar/style-menu.tiptap-toolbar-api.js'),
-			element: () => import('../components/toolbar/tiptap-toolbar-menu.element.js'),
-		},
-	},
-];
-
-const coreExtensions: Array<ManifestTiptapExtension> = [
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.RichTextEssentials',
-		name: 'Rich Text Essentials Tiptap Extension',
-		api: () => import('./core/rich-text-essentials.tiptap-api.js'),
-		weight: 1000,
-		meta: {
-			icon: 'icon-browser-window',
-			label: 'Rich Text Essentials',
-			group: '#tiptap_extGroup_formatting',
-			description: 'This is a core extension, it is always enabled by default.',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.Embed',
-		name: 'Embed Tiptap Extension',
-		api: () => import('./core/embedded-media.tiptap-api.js'),
-		meta: {
-			icon: 'icon-embed',
-			label: '#general_embed',
-			group: '#tiptap_extGroup_media',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.Link',
-		name: 'Link Tiptap Extension',
-		api: () => import('./core/link.tiptap-api.js'),
-		meta: {
-			icon: 'icon-link',
-			label: '#defaultdialogs_urlLinkPicker',
-			group: '#tiptap_extGroup_interactive',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.Figure',
-		name: 'Figure Tiptap Extension',
-		api: () => import('./core/figure.tiptap-api.js'),
-		meta: {
-			icon: 'icon-frame',
-			label: 'Figure',
-			group: '#tiptap_extGroup_media',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.Image',
-		name: 'Image Tiptap Extension',
-		api: () => import('./core/image.tiptap-api.js'),
-		meta: {
-			icon: 'icon-picture',
-			label: 'Image',
-			group: '#tiptap_extGroup_media',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Subscript',
-		name: 'Subscript Tiptap Extension',
-		api: () => import('./core/subscript.tiptap-api.js'),
-		meta: {
-			icon: 'icon-subscript',
-			label: 'Subscript',
-			group: '#tiptap_extGroup_formatting',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Superscript',
-		name: 'Superscript Tiptap Extension',
-		api: () => import('./core/superscript.tiptap-api.js'),
-		meta: {
-			icon: 'icon-superscript',
-			label: 'Superscript',
-			group: '#tiptap_extGroup_formatting',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Underline',
-		name: 'Underline Tiptap Extension',
-		api: () => import('./core/underline.tiptap-api.js'),
-		meta: {
-			icon: 'icon-underline',
-			label: 'Underline',
-			group: '#tiptap_extGroup_formatting',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.TextAlign',
-		name: 'Text Align Tiptap Extension',
-		api: () => import('./core/text-align.tiptap-api.js'),
-		meta: {
-			icon: 'icon-text-align-justify',
-			label: 'Text Align',
-			group: '#tiptap_extGroup_formatting',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.TextDirection',
-		name: 'Text Direction Tiptap Extension',
-		api: () => import('./core/text-direction.tiptap-api.js'),
-		meta: {
-			icon: 'icon-text-direction-ltr',
-			label: 'Text Direction',
-			group: '#tiptap_extGroup_formatting',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.MediaUpload',
-		name: 'Media Upload Tiptap Extension',
-		api: () => import('./core/media-upload.tiptap-api.js'),
-		meta: {
-			icon: 'icon-image-up',
-			label: 'Media Upload',
-			group: '#tiptap_extGroup_media',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.TextIndent',
-		name: 'Text Indent Tiptap Extension',
-		api: () => import('./core/text-indent.tiptap-api.js'),
-		meta: {
-			icon: 'icon-indent',
-			label: 'Text Indent',
-			group: '#tiptap_extGroup_formatting',
-		},
-	},
-	{
-		type: 'tiptapExtension',
-		alias: 'Umb.Tiptap.WordCount',
-		name: 'Word Count Tiptap Extension',
-		api: () => import('./core/word-count.tiptap-api.js'),
-		meta: {
-			icon: 'icon-speed-gauge',
-			label: 'Word Count',
-			group: '#tiptap_extGroup_interactive',
-		},
-	},
-];
-
-const toolbarExtensions: Array<UmbExtensionManifest> = [
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.SourceEditor',
-		name: 'Source Editor Tiptap Extension',
-		api: () => import('./toolbar/source-editor.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'umbSourceEditor',
-			icon: 'icon-code-xml',
-			label: '#general_viewSourceCode',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Bold',
-		name: 'Bold Tiptap Extension',
-		api: () => import('./toolbar/bold.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'bold',
-			icon: 'icon-bold',
-			label: '#buttons_bold',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Italic',
-		name: 'Italic Tiptap Extension',
-		api: () => import('./toolbar/italic.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'italic',
-			icon: 'icon-italic',
-			label: '#buttons_italic',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Underline',
-		name: 'Underline Tiptap Extension',
-		api: () => import('./toolbar/underline.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.Underline'],
-		meta: {
-			alias: 'underline',
-			icon: 'icon-underline',
-			label: 'Underline',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Strike',
-		name: 'Strike Tiptap Extension',
-		api: () => import('./toolbar/strike.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'strike',
-			icon: 'icon-strikethrough',
-			label: 'Strike',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.ClearFormatting',
-		name: 'Clear Formatting Tiptap Extension',
-		api: () => import('./toolbar/clear-formatting.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'clear-formatting',
-			icon: 'icon-clear-formatting',
-			label: 'Clear Formatting',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextAlignLeft',
-		name: 'Text Align Left Tiptap Extension',
-		api: () => import('./toolbar/text-align-left.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextAlign'],
-		meta: {
-			alias: 'text-align-left',
-			icon: 'icon-text-align-left',
-			label: 'Text Align Left',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextAlignCenter',
-		name: 'Text Align Center Tiptap Extension',
-		api: () => import('./toolbar/text-align-center.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextAlign'],
-		meta: {
-			alias: 'text-align-center',
-			icon: 'icon-text-align-center',
-			label: 'Text Align Center',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextAlignRight',
-		name: 'Text Align Right Tiptap Extension',
-		api: () => import('./toolbar/text-align-right.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextAlign'],
-		meta: {
-			alias: 'text-align-right',
-			icon: 'icon-text-align-right',
-			label: 'Text Align Right',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextAlignJustify',
-		name: 'Text Align Justify Tiptap Extension',
-		api: () => import('./toolbar/text-align-justify.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextAlign'],
-		meta: {
-			alias: 'text-align-justify',
-			icon: 'icon-text-align-justify',
-			label: 'Text Align Justify',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'colorPickerButton',
-		alias: 'Umb.Tiptap.Toolbar.TextColorBackground',
-		name: 'Text Color Background Tiptap Extension',
-		api: () => import('./toolbar/text-color-background.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'text-color-background',
-			icon: 'icon-color-bucket',
-			label: 'Background color',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'colorPickerButton',
-		alias: 'Umb.Tiptap.Toolbar.TextColorForeground',
-		name: 'Text Color Foreground Tiptap Extension',
-		api: () => import('./toolbar/text-color-foreground.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'text-color-foreground',
-			icon: 'icon-colorpicker',
-			label: 'Color',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextDirectionRtl',
-		name: 'Text Direction RTL Tiptap Extension',
-		api: () => import('./toolbar/text-direction-rtl.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextDirection'],
-		meta: {
-			alias: 'text-direction-rtl',
-			icon: 'icon-text-direction-rtl',
-			label: 'Right to left',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextDirectionLtr',
-		name: 'Text Direction LTR Tiptap Extension',
-		api: () => import('./toolbar/text-direction-ltr.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextDirection'],
-		meta: {
-			alias: 'text-direction-ltr',
-			icon: 'icon-text-direction-ltr',
-			label: 'Left to right',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Heading1',
-		name: 'Heading 1 Tiptap Extension',
-		api: () => import('./toolbar/heading1.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'heading1',
-			icon: 'icon-heading-1',
-			label: 'Heading 1',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Heading2',
-		name: 'Heading 2 Tiptap Extension',
-		api: () => import('./toolbar/heading2.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'heading2',
-			icon: 'icon-heading-2',
-			label: 'Heading 2',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Heading3',
-		name: 'Heading 3 Tiptap Extension',
-		api: () => import('./toolbar/heading3.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'heading3',
-			icon: 'icon-heading-3',
-			label: 'Heading 3',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.BulletList',
-		name: 'Bullet List Tiptap Extension',
-		api: () => import('./toolbar/bullet-list.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'bulletList',
-			icon: 'icon-bulleted-list',
-			label: '#buttons_listBullet',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.OrderedList',
-		name: 'Ordered List Tiptap Extension',
-		api: () => import('./toolbar/ordered-list.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'orderedList',
-			icon: 'icon-ordered-list',
-			label: 'Ordered List',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Anchor',
-		name: 'Anchor Tiptap Extension',
-		api: () => import('./toolbar/anchor.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'anchor',
-			icon: 'icon-anchor',
-			label: '#tiptap_anchor',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Blockquote',
-		name: 'Blockquote Tiptap Extension',
-		api: () => import('./toolbar/blockquote.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'blockquote',
-			icon: 'icon-blockquote',
-			label: 'Blockquote',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Link',
-		name: 'Link Tiptap Extension',
-		api: () => import('./toolbar/link.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.Link'],
-		meta: {
-			alias: 'umbLink',
-			icon: 'icon-link',
-			label: '#defaultdialogs_urlLinkPicker',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Unlink',
-		name: 'Unlink Tiptap Extension',
-		api: () => import('./toolbar/unlink.tiptap-toolbar-api.js'),
-		element: () => import('../components/toolbar/tiptap-toolbar-button-disabled.element.js'),
-		forExtensions: ['Umb.Tiptap.Link'],
-		meta: {
-			alias: 'unlink',
-			icon: 'icon-unlink',
-			label: 'Unlink',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.CodeBlock',
-		name: 'Code Block Tiptap Extension',
-		api: () => import('./toolbar/code-block.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'codeBlock',
-			icon: 'icon-code',
-			label: 'Code Block',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Subscript',
-		name: 'Subscript Tiptap Extension',
-		api: () => import('./toolbar/subscript.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.Subscript'],
-		meta: {
-			alias: 'subscript',
-			icon: 'icon-subscript',
-			label: 'Subscript',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Superscript',
-		name: 'Superscript Tiptap Extension',
-		api: () => import('./toolbar/superscript.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.Superscript'],
-		meta: {
-			alias: 'superscript',
-			icon: 'icon-superscript',
-			label: 'Superscript',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.HorizontalRule',
-		name: 'Horizontal Rule Tiptap Extension',
-		api: () => import('./toolbar/horizontal-rule.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'horizontalRule',
-			icon: 'icon-horizontal-rule',
-			label: 'Horizontal Rule',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Undo',
-		name: 'Undo Tiptap Extension',
-		api: () => import('./toolbar/undo.tiptap-toolbar-api.js'),
-		element: () => import('../components/toolbar/tiptap-toolbar-button-disabled.element.js'),
-		meta: {
-			alias: 'undo',
-			icon: 'icon-undo',
-			label: '#buttons_undo',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.Redo',
-		name: 'Redo Tiptap Extension',
-		api: () => import('./toolbar/redo.tiptap-toolbar-api.js'),
-		element: () => import('../components/toolbar/tiptap-toolbar-button-disabled.element.js'),
-		meta: {
-			alias: 'redo',
-			icon: 'icon-redo',
-			label: '#buttons_redo',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.MediaPicker',
-		name: 'Media Picker Tiptap Extension',
-		api: () => import('./toolbar/media-picker.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.Figure', 'Umb.Tiptap.Image'],
-		meta: {
-			alias: 'umbMedia',
-			icon: 'icon-picture',
-			label: '#general_mediaPicker',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.EmbeddedMedia',
-		name: 'Embedded Media Tiptap Extension',
-		api: () => import('./toolbar/embedded-media.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.Embed'],
-		meta: {
-			alias: 'umbEmbeddedMedia',
-			icon: 'icon-embed',
-			label: '#general_embed',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'menu',
-		alias: 'Umb.Tiptap.Toolbar.FontFamily',
-		name: 'Font Family Tiptap Extension',
-		api: () => import('./toolbar/font-family.tiptap-toolbar-api.js'),
-		items: [
-			{ label: 'Sans serif', appearance: { style: 'font-family: sans-serif;' }, data: 'sans-serif' },
-			{ label: 'Serif', appearance: { style: 'font-family: serif;' }, data: 'serif' },
-			{ label: 'Monospace', appearance: { style: 'font-family: monospace;' }, data: 'monospace' },
-			{ label: 'Cursive', appearance: { style: 'font-family: cursive;' }, data: 'cursive' },
-			{ label: 'Fantasy', appearance: { style: 'font-family: fantasy;' }, data: 'fantasy' },
-		],
-		meta: {
-			alias: 'umbFontFamily',
-			icon: 'icon-ruler-alt',
-			label: 'Font family',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'menu',
-		alias: 'Umb.Tiptap.Toolbar.FontSize',
-		name: 'Font Size Tiptap Extension',
-		api: () => import('./toolbar/font-size.tiptap-toolbar-api.js'),
-		items: [
-			{ label: '8pt', data: '8pt' },
-			{ label: '10pt', data: '10pt' },
-			{ label: '12pt', data: '12pt' },
-			{ label: '14pt', data: '14pt' },
-			{ label: '16pt', data: '16pt' },
-			{ label: '18pt', data: '18pt' },
-			{ label: '24pt', data: '24pt' },
-			{ label: '26pt', data: '26pt' },
-			{ label: '48pt', data: '48pt' },
-		],
-		meta: {
-			alias: 'umbFontSize',
-			icon: 'icon-ruler',
-			label: 'Font size',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.CharacterMap',
-		name: 'Character Map Tiptap Extension',
-		api: () => import('./toolbar/character-map.tiptap-toolbar-api.js'),
-		meta: {
-			alias: 'umbCharacterMap',
-			icon: 'icon-omega',
-			label: '#tiptap_charmap',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextIndent',
-		name: 'Text Indent Tiptap Extension',
-		api: () => import('./toolbar/text-indent.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextIndent'],
-		meta: {
-			alias: 'indent',
-			icon: 'icon-indent',
-			label: 'Indent',
-		},
-	},
-	{
-		type: 'tiptapToolbarExtension',
-		kind: 'button',
-		alias: 'Umb.Tiptap.Toolbar.TextOutdent',
-		name: 'Text Outdent Tiptap Extension',
-		api: () => import('./toolbar/text-outdent.tiptap-toolbar-api.js'),
-		forExtensions: ['Umb.Tiptap.TextIndent'],
-		meta: {
-			alias: 'outdent',
-			icon: 'icon-outdent',
-			label: 'Outdent',
-		},
-	},
-];
+const kinds = [buttonKind, colorPickerButton, menuButton, styleMenuKind];
 
 export const manifests = [
 	...kinds,
-	...coreExtensions,
-	...statusbarExtensions,
-	...toolbarExtensions,
-	...blockExtensions,
-	...styleSelectExtensions,
-	...tableExtensions,
+	...anchor,
+	...block,
+	...blockquote,
+	...bold,
+	...bulletList,
+	...characterMap,
+	...clearFormatting,
+	...codeBlock,
+	...core,
+	...elementPath,
+	...embeddedMedia,
+	...figure,
+	...fontFamily,
+	...fontSize,
+	...heading,
+	...horizontalRule,
+	...htmlAttrClass,
+	...htmlAttrDataset,
+	...htmlAttrId,
+	...htmlAttrStyle,
+	...htmlTagDiv,
+	...htmlTagSpan,
+	...image,
+	...italic,
+	...link,
+	...mediaPicker,
+	...mediaUpload,
+	...orderedList,
+	...strike,
+	...styleSelect,
+	...subscript,
+	...superscript,
+	...table,
+	...textAlign,
+	...textColor,
+	...textDirection,
+	...textIndent,
+	...trailingNode,
+	...underline,
+	...undoRedo,
+	...viewSource,
+	...wordCount,
 ];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-picker/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-picker/manifests.ts
new file mode 100644
index 000000000000..cf0918261dd5
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-picker/manifests.ts
@@ -0,0 +1,15 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.MediaPicker',
+		name: 'Media Picker Tiptap Toolbar Extension',
+		api: () => import('./media-picker.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Figure', 'Umb.Tiptap.Image'],
+		meta: {
+			alias: 'umbMedia',
+			icon: 'icon-picture',
+			label: '#general_mediaPicker',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/media-picker.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-picker/media-picker.tiptap-toolbar-api.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/media-picker.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-picker/media-picker.tiptap-toolbar-api.ts
index 0963c86be5cf..7971a4254097 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/media-picker.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-picker/media-picker.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import { getGuidFromUdi, imageSize } from '@umbraco-cms/backoffice/utils';
 import { ImageCropModeModel } from '@umbraco-cms/backoffice/external/backend-api';
 import { UmbImagingRepository } from '@umbraco-cms/backoffice/imaging';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-upload/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-upload/manifests.ts
new file mode 100644
index 000000000000..25e3183c5f87
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-upload/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.MediaUpload',
+		name: 'Media Upload Tiptap Extension',
+		api: () => import('./media-upload.tiptap-api.js'),
+		meta: {
+			icon: 'icon-image-up',
+			label: 'Media Upload',
+			group: '#tiptap_extGroup_media',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/media-upload.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-upload/media-upload.tiptap-api.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/media-upload.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-upload/media-upload.tiptap-api.ts
index 0a848e16763b..46dfaa0620a0 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/media-upload.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/media-upload/media-upload.tiptap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import type { UmbTiptapExtensionArgs } from '../types.js';
 import { imageSize } from '@umbraco-cms/backoffice/utils';
 import { Extension } from '@umbraco-cms/backoffice/external/tiptap';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/manifests.ts
new file mode 100644
index 000000000000..089dc6936547
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.OrderedList',
+		name: 'Ordered List Tiptap Extension',
+		api: () => import('./ordered-list.tiptap-api.js'),
+		meta: {
+			icon: 'icon-ordered-list',
+			label: 'Ordered List',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.OrderedList',
+		name: 'Ordered List Tiptap Toolbar Extension',
+		api: () => import('./ordered-list.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.OrderedList'],
+		meta: {
+			alias: 'orderedList',
+			icon: 'icon-ordered-list',
+			label: 'Ordered List',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/ordered-list.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/ordered-list.tiptap-api.ts
new file mode 100644
index 000000000000..8583b4e860c5
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/ordered-list.tiptap-api.ts
@@ -0,0 +1,16 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { css } from '@umbraco-cms/backoffice/external/lit';
+import { ListItem, OrderedList } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapOrderedListExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [ListItem, OrderedList];
+
+	override getStyles = () => css`
+		li {
+			> p {
+				margin: 0;
+				padding: 0;
+			}
+		}
+	`;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/ordered-list.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/ordered-list.tiptap-toolbar-api.ts
similarity index 82%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/ordered-list.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/ordered-list.tiptap-toolbar-api.ts
index 26956cfcde6b..77a3932eebaa 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/ordered-list.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/ordered-list/ordered-list.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import { OrderedList, ListItem } from '@umbraco-cms/backoffice/external/tiptap';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/manifests.ts
new file mode 100644
index 000000000000..8cd410645ab7
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/manifests.ts
@@ -0,0 +1,26 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.Strike',
+		name: 'Strike Tiptap Extension',
+		api: () => import('./strike.tiptap-api.js'),
+		meta: {
+			icon: 'icon-strikethrough',
+			label: 'Strike',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Strike',
+		name: 'Strike Tiptap Toolbar Extension',
+		api: () => import('./strike.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Strike'],
+		meta: {
+			alias: 'strike',
+			icon: 'icon-strikethrough',
+			label: 'Strike',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/strike.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/strike.tiptap-api.ts
new file mode 100644
index 000000000000..7d77e786f3ac
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/strike.tiptap-api.ts
@@ -0,0 +1,6 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { Strike } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapStrikeExtensionApi extends UmbTiptapExtensionApiBase {
+	getTiptapExtensions = () => [Strike];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/strike.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/strike.tiptap-toolbar-api.ts
similarity index 74%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/strike.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/strike.tiptap-toolbar-api.ts
index 7062ab000efd..a006983323b0 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/strike.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/strike/strike.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarStrikeExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.kind.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.kind.ts
new file mode 100644
index 000000000000..f211fc9135e9
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.kind.ts
@@ -0,0 +1,12 @@
+import type { UmbExtensionManifestKind } from '@umbraco-cms/backoffice/extension-registry';
+
+export const manifest: UmbExtensionManifestKind = {
+	type: 'kind',
+	alias: 'Umb.Kind.TiptapToolbar.StyleMenu',
+	matchKind: 'styleMenu',
+	matchType: 'tiptapToolbarExtension',
+	manifest: {
+		api: () => import('./style-menu.tiptap-toolbar-api.js'),
+		element: () => import('../../components/toolbar/tiptap-toolbar-menu.element.js'),
+	},
+};
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/style-menu.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts
similarity index 96%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/style-menu.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts
index 381607675acd..9d68f0e176f7 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/toolbar/style-menu.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-menu/style-menu.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../../extensions/base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { MetaTiptapToolbarStyleMenuItem } from '../../extensions/types.js';
 import type { ChainedCommands, Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-select/style-select.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-select/style-select.tiptap-toolbar-api.ts
index d67746a41267..06bcc023d4c9 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-select/style-select.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/style-select/style-select.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import UmbTiptapToolbarStyleMenuApi from '../../components/toolbar/style-menu.tiptap-toolbar-api.js';
+import UmbTiptapToolbarStyleMenuApi from '../style-menu/style-menu.tiptap-toolbar-api.js';
 
 /** @deprecated No longer used internally. This class will be removed in Umbraco 17. [LK] */
 export default class UmbTiptapToolbarStyleSelectExtensionApi extends UmbTiptapToolbarStyleMenuApi {}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/manifests.ts
new file mode 100644
index 000000000000..7742d8bd8101
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/manifests.ts
@@ -0,0 +1,27 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Subscript',
+		name: 'Subscript Tiptap Extension',
+		api: () => import('./subscript.tiptap-api.js'),
+		meta: {
+			icon: 'icon-subscript',
+			label: 'Subscript',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Subscript',
+		name: 'Subscript Tiptap Toolbar Extension',
+		api: () => import('./subscript.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Subscript'],
+		meta: {
+			alias: 'subscript',
+			icon: 'icon-subscript',
+			label: 'Subscript',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/subscript.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/subscript.tiptap-api.ts
similarity index 71%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/subscript.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/subscript.tiptap-api.ts
index be83a3236ed8..d1d14d23d537 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/subscript.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/subscript.tiptap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { Subscript } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapBoldExtensionApi extends UmbTiptapExtensionApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/subscript.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/subscript.tiptap-toolbar-api.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/subscript.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/subscript.tiptap-toolbar-api.ts
index d78312e01e12..90a5d9e3ec1f 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/subscript.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/subscript/subscript.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarSubscriptExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/manifests.ts
new file mode 100644
index 000000000000..818216ae0701
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/manifests.ts
@@ -0,0 +1,27 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Superscript',
+		name: 'Superscript Tiptap Extension',
+		api: () => import('./superscript.tiptap-api.js'),
+		meta: {
+			icon: 'icon-superscript',
+			label: 'Superscript',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Superscript',
+		name: 'Superscript Tiptap Toolbar Extension',
+		api: () => import('./superscript.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Superscript'],
+		meta: {
+			alias: 'superscript',
+			icon: 'icon-superscript',
+			label: 'Superscript',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/superscript.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/superscript.tiptap-api.ts
similarity index 72%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/superscript.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/superscript.tiptap-api.ts
index e7757efc5df4..ec72e4be6f8f 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/superscript.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/superscript.tiptap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { Superscript } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapBoldExtensionApi extends UmbTiptapExtensionApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/superscript.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/superscript.tiptap-toolbar-api.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/superscript.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/superscript.tiptap-toolbar-api.ts
index 5da21dc34d96..38141e2a2046 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/superscript.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/superscript/superscript.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarSuperscriptExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/actions/table-properties.action.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/actions/table-properties.action.ts
index 1e78982cac1a..64add0ac0517 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/actions/table-properties.action.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/actions/table-properties.action.ts
@@ -1,6 +1,6 @@
 import { UmbTiptapMenuItemActionApi } from '../../../components/menu/tiptap-menu-item-api-base.js';
 import { UMB_TIPTAP_RTE_CONTEXT } from '../../../contexts/tiptap-rte.context-token.js';
-import { UMB_TIPTAP_TABLE_PROPERTIES_MODAL } from '../components/table-properties-modal.token.js';
+import { UMB_TIPTAP_TABLE_PROPERTIES_MODAL } from '../modals/table-properties-modal.token.js';
 import { UMB_MODAL_MANAGER_CONTEXT } from '@umbraco-cms/backoffice/modal';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-column-menu.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-column-menu.element.ts
index abd8c29c9aef..a8b434b62a68 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-column-menu.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-column-menu.element.ts
@@ -2,7 +2,7 @@ import { css, customElement, html, property } from '@umbraco-cms/backoffice/exte
 import { UmbLitElement } from '@umbraco-cms/backoffice/lit-element';
 import type { Editor, UmbTiptapBubbleMenuElement } from '@umbraco-cms/backoffice/external/tiptap';
 
-/** @deprecated No longer used internally. This will be removed in Umbraco 18. [LK] */
+/** @deprecated No longer used internally. This will be removed in Umbraco 17. [LK] */
 @customElement('umb-tiptap-table-column-menu')
 export class UmbTiptapTableColumnMenuElement extends UmbLitElement implements UmbTiptapBubbleMenuElement {
 	@property({ attribute: false })
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-row-menu.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-row-menu.element.ts
index 7b858b5c7710..13e38c867ad9 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-row-menu.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-row-menu.element.ts
@@ -2,7 +2,7 @@ import { css, customElement, html, property } from '@umbraco-cms/backoffice/exte
 import { UmbLitElement } from '@umbraco-cms/backoffice/lit-element';
 import type { Editor, UmbTiptapBubbleMenuElement } from '@umbraco-cms/backoffice/external/tiptap';
 
-/** @deprecated No longer used internally. This will be removed in Umbraco 18. [LK] */
+/** @deprecated No longer used internally. This will be removed in Umbraco 17. [LK] */
 @customElement('umb-tiptap-table-row-menu')
 export class UmbTiptapTableRowMenuElement extends UmbLitElement implements UmbTiptapBubbleMenuElement {
 	@property({ attribute: false })
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/constants.ts
new file mode 100644
index 000000000000..ea358318ca28
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/constants.ts
@@ -0,0 +1 @@
+export * from './modals/constants.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/index.ts
index cda941411e06..9e897c4aa454 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/index.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/index.ts
@@ -1 +1 @@
-export * from './components/table-properties-modal.token.js';
+export * from './modals/index.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/manifests.ts
index b34e0a92b47b..e0340bbe5f91 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/manifests.ts
@@ -1,4 +1,4 @@
-import { UMB_TIPTAP_TABLE_PROPERTIES_MODAL_ALIAS } from './components/constants.js';
+import { UMB_TIPTAP_TABLE_PROPERTIES_MODAL_ALIAS } from './modals/constants.js';
 
 const UMB_MENU_TIPTAP_TABLE_ALIAS = 'Umb.Menu.Tiptap.Table';
 const UMB_MENU_TIPTAP_TABLE_COLUMN_ALIAS = 'Umb.Menu.Tiptap.TableColumn';
@@ -10,7 +10,7 @@ const modals: Array<UmbExtensionManifest> = [
 		type: 'modal',
 		alias: UMB_TIPTAP_TABLE_PROPERTIES_MODAL_ALIAS,
 		name: 'Tiptap Table Properties Modal',
-		element: () => import('./components/table-properties-modal.element.js'),
+		element: () => import('./modals/table-properties-modal.element.js'),
 	},
 ];
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/constants.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/constants.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/constants.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/index.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/index.ts
new file mode 100644
index 000000000000..037b30057cea
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/index.ts
@@ -0,0 +1 @@
+export * from './table-properties-modal.token.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-properties-modal.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/table-properties-modal.element.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-properties-modal.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/table-properties-modal.element.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-properties-modal.token.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/table-properties-modal.token.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-properties-modal.token.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/modals/table-properties-modal.token.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-api.ts
index abb4359625b8..4cb3a7e53edf 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-api.ts
@@ -1,10 +1,11 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { css } from '@umbraco-cms/backoffice/external/lit';
 import { UmbTable, UmbTableHeader, UmbTableRow, UmbTableCell } from '@umbraco-cms/backoffice/external/tiptap';
 
 import '../../components/menu/tiptap-menu.element.js';
 
 export default class UmbTiptapTableExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
 	getTiptapExtensions = () => [UmbTable, UmbTableHeader, UmbTableRow, UmbTableCell];
 
 	override getStyles = () => css`
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-toolbar-api.ts
index e2ef0be5c3c0..d9bd0b95538d 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/table.tiptap-toolbar-api.ts
@@ -1,7 +1,7 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
-export class UmbTiptapToolbarTableExtensionApi extends UmbTiptapToolbarElementApiBase {
+export default class UmbTiptapToolbarTableExtensionApi extends UmbTiptapToolbarElementApiBase {
 	override isActive(editor?: Editor, item?: unknown) {
 		if (!item) return super.isActive(editor);
 		return false;
@@ -9,5 +9,3 @@ export class UmbTiptapToolbarTableExtensionApi extends UmbTiptapToolbarElementAp
 
 	override execute() {}
 }
-
-export { UmbTiptapToolbarTableExtensionApi as api };
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/manifests.ts
new file mode 100644
index 000000000000..fce382bce002
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/manifests.ts
@@ -0,0 +1,65 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.TextAlign',
+		name: 'Text Align Tiptap Extension',
+		api: () => import('./text-align.tiptap-api.js'),
+		meta: {
+			icon: 'icon-text-align-justify',
+			label: 'Text Align',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextAlignLeft',
+		name: 'Text Align Left Tiptap Toolbar Extension',
+		api: () => import('./text-align-left.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextAlign'],
+		meta: {
+			alias: 'text-align-left',
+			icon: 'icon-text-align-left',
+			label: 'Text Align Left',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextAlignCenter',
+		name: 'Text Align Center Tiptap Toolbar Extension',
+		api: () => import('./text-align-center.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextAlign'],
+		meta: {
+			alias: 'text-align-center',
+			icon: 'icon-text-align-center',
+			label: 'Text Align Center',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextAlignRight',
+		name: 'Text Align Right Tiptap Toolbar Extension',
+		api: () => import('./text-align-right.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextAlign'],
+		meta: {
+			alias: 'text-align-right',
+			icon: 'icon-text-align-right',
+			label: 'Text Align Right',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextAlignJustify',
+		name: 'Text Align Justify Tiptap Toolbar Extension',
+		api: () => import('./text-align-justify.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextAlign'],
+		meta: {
+			alias: 'text-align-justify',
+			icon: 'icon-text-align-justify',
+			label: 'Text Align Justify',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-center.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-center.tiptap-toolbar-api.ts
similarity index 84%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-center.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-center.tiptap-toolbar-api.ts
index f9a48e1b9fa0..314a82b8c9cc 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-center.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-center.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextAlignCenterExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-justify.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-justify.tiptap-toolbar-api.ts
similarity index 84%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-justify.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-justify.tiptap-toolbar-api.ts
index 584619954ee0..5b986d8d8d26 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-justify.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-justify.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextAlignJustifyExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-left.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-left.tiptap-toolbar-api.ts
similarity index 84%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-left.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-left.tiptap-toolbar-api.ts
index 172ccb785e54..308e054c3a22 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-left.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-left.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextAlignLeftExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-right.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-right.tiptap-toolbar-api.ts
similarity index 84%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-right.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-right.tiptap-toolbar-api.ts
index 5a1032395b4e..b5e296a59279 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-align-right.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align-right.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextAlignRightExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-align.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align.tiptap-api.ts
similarity index 80%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-align.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align.tiptap-api.ts
index 3d2598d5e3c2..a6db738a3a96 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-align.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-align/text-align.tiptap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { TextAlign } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapTextAlignExtensionApi extends UmbTiptapExtensionApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/manifests.ts
new file mode 100644
index 000000000000..3d5d5ff91318
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/manifests.ts
@@ -0,0 +1,28 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'colorPickerButton',
+		alias: 'Umb.Tiptap.Toolbar.TextColorBackground',
+		name: 'Text Color Background Tiptap Toolbar Extension',
+		api: () => import('./text-color-background.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.HtmlAttributeStyle', 'Umb.Tiptap.HtmlTagSpan'],
+		meta: {
+			alias: 'text-color-background',
+			icon: 'icon-color-bucket',
+			label: 'Background color',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'colorPickerButton',
+		alias: 'Umb.Tiptap.Toolbar.TextColorForeground',
+		name: 'Text Color Foreground Tiptap Toolbar Extension',
+		api: () => import('./text-color-foreground.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.HtmlAttributeStyle', 'Umb.Tiptap.HtmlTagSpan'],
+		meta: {
+			alias: 'text-color-foreground',
+			icon: 'icon-colorpicker',
+			label: 'Color',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-color-background.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/text-color-background.tiptap-toolbar-api.ts
similarity index 79%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-color-background.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/text-color-background.tiptap-toolbar-api.ts
index 75b53fba9a2b..4af0aa442918 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-color-background.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/text-color-background.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextColorBackgroundExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-color-foreground.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/text-color-foreground.tiptap-toolbar-api.ts
similarity index 78%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-color-foreground.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/text-color-foreground.tiptap-toolbar-api.ts
index 41ac8e82f502..5c023a789e60 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-color-foreground.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-color/text-color-foreground.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextColorForegroundExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/manifests.ts
new file mode 100644
index 000000000000..49bdede2e759
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/manifests.ts
@@ -0,0 +1,39 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.TextDirection',
+		name: 'Text Direction Tiptap Extension',
+		api: () => import('./text-direction.tiptap-api.js'),
+		meta: {
+			icon: 'icon-text-direction-ltr',
+			label: 'Text Direction',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextDirectionRtl',
+		name: 'Text Direction RTL Tiptap Toolbar Extension',
+		api: () => import('./text-direction-rtl.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextDirection'],
+		meta: {
+			alias: 'text-direction-rtl',
+			icon: 'icon-text-direction-rtl',
+			label: 'Right to left',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextDirectionLtr',
+		name: 'Text Direction LTR Tiptap Toolbar Extension',
+		api: () => import('./text-direction-ltr.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextDirection'],
+		meta: {
+			alias: 'text-direction-ltr',
+			icon: 'icon-text-direction-ltr',
+			label: 'Left to right',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-direction-ltr.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction-ltr.tiptap-toolbar-api.ts
similarity index 85%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-direction-ltr.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction-ltr.tiptap-toolbar-api.ts
index 224146f8a4e9..b3d7c88d2f5e 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-direction-ltr.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction-ltr.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextDirectionLtrExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-direction-rtl.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction-rtl.tiptap-toolbar-api.ts
similarity index 84%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-direction-rtl.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction-rtl.tiptap-toolbar-api.ts
index 45e5b494145b..bf4631769d27 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-direction-rtl.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction-rtl.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextDirectionRtlExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-direction.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction.tiptap-api.ts
similarity index 69%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-direction.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction.tiptap-api.ts
index 504a59455ef0..c124f6b82ee4 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-direction.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-direction/text-direction.tiptap-api.ts
@@ -1,8 +1,9 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { TextDirection } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapTextDirectionExtensionApi extends UmbTiptapExtensionApiBase {
 	getTiptapExtensions = () => [
+		// eslint-disable-next-line @typescript-eslint/no-deprecated
 		TextDirection.configure({
 			types: ['heading', 'paragraph', 'blockquote', 'orderedList', 'bulletList'],
 		}),
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/manifests.ts
new file mode 100644
index 000000000000..9d0b6c3ee978
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/manifests.ts
@@ -0,0 +1,39 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.TextIndent',
+		name: 'Text Indent Tiptap Extension',
+		api: () => import('./text-indent.tiptap-api.js'),
+		meta: {
+			icon: 'icon-indent',
+			label: 'Text Indent',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextIndent',
+		name: 'Text Indent Tiptap Toolbar Extension',
+		api: () => import('./text-indent.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextIndent'],
+		meta: {
+			alias: 'indent',
+			icon: 'icon-indent',
+			label: 'Indent',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.TextOutdent',
+		name: 'Text Outdent Tiptap Toolbar Extension',
+		api: () => import('./text-outdent.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.TextIndent'],
+		meta: {
+			alias: 'outdent',
+			icon: 'icon-outdent',
+			label: 'Outdent',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-indent.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-indent.tiptap-api.ts
similarity index 69%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-indent.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-indent.tiptap-api.ts
index 407729d6be0b..56f87e710d67 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/text-indent.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-indent.tiptap-api.ts
@@ -1,8 +1,9 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { TextIndent } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapTextIndentExtensionApi extends UmbTiptapExtensionApiBase {
 	getTiptapExtensions = () => [
+		// eslint-disable-next-line @typescript-eslint/no-deprecated
 		TextIndent.configure({
 			types: ['div', 'heading', 'paragraph', 'blockquote', 'listItem', 'orderedList', 'bulletList'],
 		}),
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-indent.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-indent.tiptap-toolbar-api.ts
similarity index 74%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-indent.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-indent.tiptap-toolbar-api.ts
index 31950ba778d2..c0f8791f0e7c 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-indent.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-indent.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextIndentExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-outdent.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-outdent.tiptap-toolbar-api.ts
similarity index 74%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-outdent.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-outdent.tiptap-toolbar-api.ts
index 2c1c0167bdde..a11aa01e7c10 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/text-outdent.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/text-indent/text-outdent.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarTextOutdentExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-extension-api-base.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-extension-api-base.ts
new file mode 100644
index 000000000000..fd34d161d780
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-extension-api-base.ts
@@ -0,0 +1,35 @@
+import type { ManifestTiptapExtension, UmbTiptapExtensionApi, UmbTiptapExtensionArgs } from './types.js';
+import { UmbControllerBase } from '@umbraco-cms/backoffice/class-api';
+import type { CSSResultGroup } from '@umbraco-cms/backoffice/external/lit';
+import type { Editor, Extension, Mark, Node } from '@umbraco-cms/backoffice/external/tiptap';
+
+export abstract class UmbTiptapExtensionApiBase extends UmbControllerBase implements UmbTiptapExtensionApi {
+	/**
+	 * The manifest for the extension.
+	 */
+	manifest?: ManifestTiptapExtension;
+
+	/**
+	 * The editor instance.
+	 */
+	protected _editor?: Editor;
+
+	/**
+	 * @inheritdoc
+	 */
+	setEditor(editor: Editor): void {
+		this._editor = editor;
+	}
+
+	/**
+	 * @inheritdoc
+	 */
+	getStyles(): CSSResultGroup | null | undefined {
+		return null;
+	}
+
+	/**
+	 * @inheritdoc
+	 */
+	abstract getTiptapExtensions(args?: UmbTiptapExtensionArgs): Array<Extension | Mark | Node>;
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-button.kind.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-button.kind.ts
new file mode 100644
index 000000000000..00292b0421fb
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-button.kind.ts
@@ -0,0 +1,11 @@
+import type { UmbExtensionManifestKind } from '@umbraco-cms/backoffice/extension-registry';
+
+export const manifest: UmbExtensionManifestKind = {
+	type: 'kind',
+	alias: 'Umb.Kind.TiptapToolbar.Button',
+	matchKind: 'button',
+	matchType: 'tiptapToolbarExtension',
+	manifest: {
+		element: () => import('../components/toolbar/tiptap-toolbar-button.element.js'),
+	},
+};
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-color-picker-button.kind.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-color-picker-button.kind.ts
new file mode 100644
index 000000000000..dfb1bca4ede9
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-color-picker-button.kind.ts
@@ -0,0 +1,11 @@
+import type { UmbExtensionManifestKind } from '@umbraco-cms/backoffice/extension-registry';
+
+export const manifest: UmbExtensionManifestKind = {
+	type: 'kind',
+	alias: 'Umb.Kind.TiptapToolbar.ColorPickerButton',
+	matchKind: 'colorPickerButton',
+	matchType: 'tiptapToolbarExtension',
+	manifest: {
+		element: () => import('../components/toolbar/tiptap-toolbar-color-picker-button.element.js'),
+	},
+};
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/base.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-element-api-base.ts
similarity index 66%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/base.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-element-api-base.ts
index 7a2b218b3e0a..012a5f2ec7d5 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/base.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-element-api-base.ts
@@ -1,46 +1,8 @@
-import type {
-	ManifestTiptapExtension,
-	ManifestTiptapToolbarExtension,
-	UmbTiptapExtensionApi,
-	UmbTiptapExtensionArgs,
-	UmbTiptapToolbarElementApi,
-} from './types.js';
+import type { ManifestTiptapToolbarExtension, UmbTiptapToolbarElementApi } from './types.js';
 import { UmbControllerBase } from '@umbraco-cms/backoffice/class-api';
-import type { CSSResultGroup } from '@umbraco-cms/backoffice/external/lit';
-import type { Editor, Extension, Mark, Node } from '@umbraco-cms/backoffice/external/tiptap';
+import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 import type { UmbPropertyEditorConfigCollection } from '@umbraco-cms/backoffice/property-editor';
 
-export abstract class UmbTiptapExtensionApiBase extends UmbControllerBase implements UmbTiptapExtensionApi {
-	/**
-	 * The manifest for the extension.
-	 */
-	manifest?: ManifestTiptapExtension;
-
-	/**
-	 * The editor instance.
-	 */
-	protected _editor?: Editor;
-
-	/**
-	 * @inheritdoc
-	 */
-	setEditor(editor: Editor): void {
-		this._editor = editor;
-	}
-
-	/**
-	 * @inheritdoc
-	 */
-	getStyles(): CSSResultGroup | null | undefined {
-		return null;
-	}
-
-	/**
-	 * @inheritdoc
-	 */
-	abstract getTiptapExtensions(args?: UmbTiptapExtensionArgs): Array<Extension | Mark | Node>;
-}
-
 export abstract class UmbTiptapToolbarElementApiBase extends UmbControllerBase implements UmbTiptapToolbarElementApi {
 	#enabledExtensions?: Array<string>;
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-menu.kind.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-menu.kind.ts
new file mode 100644
index 000000000000..bb69bc7a0986
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/tiptap-toolbar-menu.kind.ts
@@ -0,0 +1,11 @@
+import type { UmbExtensionManifestKind } from '@umbraco-cms/backoffice/extension-registry';
+
+export const manifest: UmbExtensionManifestKind = {
+	type: 'kind',
+	alias: 'Umb.Kind.TiptapToolbar.Menu',
+	matchKind: 'menu',
+	matchType: 'tiptapToolbarExtension',
+	manifest: {
+		element: () => import('../components/toolbar/tiptap-toolbar-menu.element.js'),
+	},
+};
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/trailing-node/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/trailing-node/manifests.ts
new file mode 100644
index 000000000000..6b091e0d2bf7
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/trailing-node/manifests.ts
@@ -0,0 +1,13 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.TrailingNode',
+		name: 'Trailing Node Tiptap Extension',
+		api: () => import('./trailing-node.tiptap-api.js'),
+		meta: {
+			icon: 'icon-page-down',
+			label: 'Trailing Node',
+			group: '#tiptap_extGroup_interactive',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/trailing-node/trailing-node.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/trailing-node/trailing-node.tiptap-api.ts
new file mode 100644
index 000000000000..f476e59d6851
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/trailing-node/trailing-node.tiptap-api.ts
@@ -0,0 +1,7 @@
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
+import { TrailingNode } from '@umbraco-cms/backoffice/external/tiptap';
+
+export default class UmbTiptapTrailingNodeExtensionApi extends UmbTiptapExtensionApiBase {
+	// eslint-disable-next-line @typescript-eslint/no-deprecated
+	getTiptapExtensions = () => [TrailingNode];
+}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/manifests.ts
new file mode 100644
index 000000000000..3cdaff46169a
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/manifests.ts
@@ -0,0 +1,27 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Underline',
+		name: 'Underline Tiptap Extension',
+		api: () => import('./underline.tiptap-api.js'),
+		meta: {
+			icon: 'icon-underline',
+			label: 'Underline',
+			group: '#tiptap_extGroup_formatting',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Underline',
+		name: 'Underline Tiptap Toolbar Extension',
+		api: () => import('./underline.tiptap-toolbar-api.js'),
+		forExtensions: ['Umb.Tiptap.Underline'],
+		meta: {
+			alias: 'underline',
+			icon: 'icon-underline',
+			label: 'Underline',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/underline.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/underline.tiptap-api.ts
similarity index 72%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/underline.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/underline.tiptap-api.ts
index 3946d0b25993..f5c9ba3d0b41 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/underline.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/underline.tiptap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { Underline } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapUnderlineExtensionApi extends UmbTiptapExtensionApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/underline.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/underline.tiptap-toolbar-api.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/underline.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/underline.tiptap-toolbar-api.ts
index f0c91ab0afb4..74b3a028d012 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/underline.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/underline/underline.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarUnderlineExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/manifests.ts
new file mode 100644
index 000000000000..2b5108ef686e
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/manifests.ts
@@ -0,0 +1,28 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Undo',
+		name: 'Undo Tiptap Toolbar Extension',
+		api: () => import('./undo.tiptap-toolbar-api.js'),
+		element: () => import('../../components/toolbar/tiptap-toolbar-button-disabled.element.js'),
+		meta: {
+			alias: 'undo',
+			icon: 'icon-undo',
+			label: '#buttons_undo',
+		},
+	},
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.Redo',
+		name: 'Redo Tiptap Toolbar Extension',
+		api: () => import('./redo.tiptap-toolbar-api.js'),
+		element: () => import('../../components/toolbar/tiptap-toolbar-button-disabled.element.js'),
+		meta: {
+			alias: 'redo',
+			icon: 'icon-redo',
+			label: '#buttons_redo',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/redo.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/redo.tiptap-toolbar-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/redo.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/redo.tiptap-toolbar-api.ts
index 5c6c8d9cf978..f41165d5ca6f 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/redo.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/redo.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarRedoExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/undo.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/undo.tiptap-toolbar-api.ts
similarity index 81%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/undo.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/undo.tiptap-toolbar-api.ts
index 8045536bf7c0..476ab16e8844 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/undo.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/undo-redo/undo.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarUndoExtensionApi extends UmbTiptapToolbarElementApiBase {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/view-source/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/view-source/manifests.ts
new file mode 100644
index 000000000000..e5e191edd067
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/view-source/manifests.ts
@@ -0,0 +1,14 @@
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapToolbarExtension',
+		kind: 'button',
+		alias: 'Umb.Tiptap.Toolbar.SourceEditor',
+		name: 'Source Editor Tiptap Toolbar Extension',
+		api: () => import('./source-editor.tiptap-toolbar-api.js'),
+		meta: {
+			alias: 'umbSourceEditor',
+			icon: 'icon-code-xml',
+			label: '#general_viewSourceCode',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/source-editor.tiptap-toolbar-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/view-source/source-editor.tiptap-toolbar-api.ts
similarity index 90%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/source-editor.tiptap-toolbar-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/view-source/source-editor.tiptap-toolbar-api.ts
index 3d5593ab059f..c14d35e76cda 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/toolbar/source-editor.tiptap-toolbar-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/view-source/source-editor.tiptap-toolbar-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapToolbarElementApiBase } from '../base.js';
+import { UmbTiptapToolbarElementApiBase } from '../tiptap-toolbar-element-api-base.js';
 import { UMB_CODE_EDITOR_MODAL } from '@umbraco-cms/backoffice/code-editor';
 import { umbOpenModal } from '@umbraco-cms/backoffice/modal';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/manifests.ts
similarity index 57%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/manifests.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/manifests.ts
index 40825436c960..d563e0891c0a 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/manifests.ts
@@ -1,25 +1,25 @@
-export const manifests: Array<UmbExtensionManifest> = [
-	{
-		type: 'tiptapStatusbarExtension',
-		alias: 'Umb.Tiptap.Statusbar.WordCount',
-		name: 'Word Count Tiptap Statusbar Extension',
-		element: () => import('./word-count.tiptap-statusbar-element.js'),
-		forExtensions: ['Umb.Tiptap.WordCount'],
-		meta: {
-			alias: 'wordCount',
-			icon: 'icon-speed-gauge',
-			label: 'Word Count',
-		},
-	},
-	{
-		type: 'tiptapStatusbarExtension',
-		alias: 'Umb.Tiptap.Statusbar.ElementPath',
-		name: 'Element Path Tiptap Statusbar Extension',
-		element: () => import('./element-path.tiptap-statusbar-element.js'),
-		meta: {
-			alias: 'elementPath',
-			icon: 'icon-map-alt',
-			label: 'Element Path',
-		},
-	},
-];
+export const manifests: Array<UmbExtensionManifest> = [
+	{
+		type: 'tiptapExtension',
+		alias: 'Umb.Tiptap.WordCount',
+		name: 'Word Count Tiptap Extension',
+		api: () => import('./word-count.tiptap-api.js'),
+		meta: {
+			icon: 'icon-speed-gauge',
+			label: 'Word Count',
+			group: '#tiptap_extGroup_interactive',
+		},
+	},
+	{
+		type: 'tiptapStatusbarExtension',
+		alias: 'Umb.Tiptap.Statusbar.WordCount',
+		name: 'Word Count Tiptap Statusbar Extension',
+		element: () => import('./word-count.tiptap-statusbar-element.js'),
+		forExtensions: ['Umb.Tiptap.WordCount'],
+		meta: {
+			alias: 'wordCount',
+			icon: 'icon-speed-gauge',
+			label: 'Word Count',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/word-count.tiptap-api.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/word-count.tiptap-api.ts
similarity index 80%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/word-count.tiptap-api.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/word-count.tiptap-api.ts
index 1a2bb5cce555..3ad80c0aa7b1 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/core/word-count.tiptap-api.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/word-count.tiptap-api.ts
@@ -1,4 +1,4 @@
-import { UmbTiptapExtensionApiBase } from '../base.js';
+import { UmbTiptapExtensionApiBase } from '../tiptap-extension-api-base.js';
 import { css } from '@umbraco-cms/backoffice/external/lit';
 import { CharacterCount } from '@umbraco-cms/backoffice/external/tiptap';
 
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/word-count.tiptap-statusbar-element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/word-count.tiptap-statusbar-element.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/statusbar/word-count.tiptap-statusbar-element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/word-count/word-count.tiptap-statusbar-element.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/manifests.ts
index 18d116074096..9325da5e4fe2 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/manifests.ts
@@ -1,10 +1,5 @@
-import { manifests as components } from './components/manifests.js';
 import { manifests as extensions } from './extensions/manifests.js';
 import { manifests as propertyEditors } from './property-editors/manifests.js';
 import type { UmbExtensionManifestKind } from '@umbraco-cms/backoffice/extension-registry';
 
-export const manifests: Array<UmbExtensionManifest | UmbExtensionManifestKind> = [
-	...components,
-	...extensions,
-	...propertyEditors,
-];
+export const manifests: Array<UmbExtensionManifest | UmbExtensionManifestKind> = [...extensions, ...propertyEditors];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/constants.ts
new file mode 100644
index 000000000000..8843e66a4bc9
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/constants.ts
@@ -0,0 +1,2 @@
+export * from './statusbar-configuration/tiptap-statusbar-configuration.context-token.js';
+export * from './toolbar-configuration/tiptap-toolbar-configuration.context-token.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/extensions-configuration/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/extensions-configuration/manifests.ts
new file mode 100644
index 000000000000..eb1c1f67ebe7
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/extensions-configuration/manifests.ts
@@ -0,0 +1,15 @@
+import type { ManifestPropertyEditorUi } from '@umbraco-cms/backoffice/property-editor';
+
+export const manifests: Array<ManifestPropertyEditorUi> = [
+	{
+		type: 'propertyEditorUi',
+		alias: 'Umb.PropertyEditorUi.Tiptap.ExtensionsConfiguration',
+		name: 'Tiptap Extensions Property Editor UI',
+		element: () => import('./property-editor-ui-tiptap-extensions-configuration.element.js'),
+		meta: {
+			label: 'Tiptap Extensions Configuration',
+			icon: 'icon-autofill',
+			group: 'common',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-extensions-configuration.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/extensions-configuration/property-editor-ui-tiptap-extensions-configuration.element.ts
similarity index 94%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-extensions-configuration.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/extensions-configuration/property-editor-ui-tiptap-extensions-configuration.element.ts
index a242fd692e32..ad71fe55681f 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-extensions-configuration.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/extensions-configuration/property-editor-ui-tiptap-extensions-configuration.element.ts
@@ -1,6 +1,6 @@
 import {
-	customElement,
 	css,
+	customElement,
 	html,
 	ifDefined,
 	nothing,
@@ -100,7 +100,7 @@ export class UmbPropertyEditorUiTiptapExtensionsConfigurationElement
 
 		this.observe(umbExtensionsRegistry.byType('tiptapExtension'), (extensions) => {
 			this._extensions = extensions
-				.sort((a, b) => a.alias.localeCompare(b.alias))
+				.sort((a, b) => (b.weight || 0) - (a.weight || 0) || a.alias.localeCompare(b.alias))
 				.map((ext) => ({
 					alias: ext.alias,
 					label: ext.meta.label,
@@ -175,7 +175,11 @@ export class UmbPropertyEditorUiTiptapExtensionsConfigurationElement
 											@change=${() => this.#onClick(item)}>
 											<div class="inner">
 												${when(item.icon, () => html`<umb-icon .name=${item.icon}></umb-icon>`)}
-												<span>${this.localize.string(item.label)}</span>
+												${when(
+													item.label.startsWith('#'),
+													() => html`<span>${this.localize.string(item.label)}</span>`,
+													() => html`<umb-ufm-render inline .markdown=${item.label}></umb-ufm-render>`,
+												)}
 											</div>
 										</uui-checkbox>
 									</li>
@@ -197,7 +201,8 @@ export class UmbPropertyEditorUiTiptapExtensionsConfigurationElement
 			}
 
 			.group {
-				width: calc((100% - 2rem) / 3);
+				min-width: 180px;
+				width: calc((100% - 3rem) / 4);
 
 				ul {
 					list-style: none;
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/manifests.ts
index 734619f0cf12..9d5bf7c39277 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/manifests.ts
@@ -1,5 +1,12 @@
-// eslint-disable-next-line local-rules/no-relative-import-to-import-map-module
-import { manifests as tiptapManifests } from './tiptap/manifests.js';
+import { manifests as extensionsConfiguration } from './extensions-configuration/manifests.js';
+import { manifests as statusbarConfiguration } from './statusbar-configuration/manifests.js';
+import { manifests as tiptapRte } from './tiptap-rte/manifests.js';
+import { manifests as toolbarConfiguration } from './toolbar-configuration/manifests.js';
 import type { ManifestPropertyEditorUi } from '@umbraco-cms/backoffice/property-editor';
 
-export const manifests: Array<ManifestPropertyEditorUi> = [...tiptapManifests];
+export const manifests: Array<ManifestPropertyEditorUi> = [
+	...extensionsConfiguration,
+	...statusbarConfiguration,
+	...tiptapRte,
+	...toolbarConfiguration,
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/manifests.ts
new file mode 100644
index 000000000000..ab3d182f7baa
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/manifests.ts
@@ -0,0 +1,15 @@
+import type { ManifestPropertyEditorUi } from '@umbraco-cms/backoffice/property-editor';
+
+export const manifests: Array<ManifestPropertyEditorUi> = [
+	{
+		type: 'propertyEditorUi',
+		alias: 'Umb.PropertyEditorUi.Tiptap.StatusbarConfiguration',
+		name: 'Tiptap Statusbar Property Editor UI',
+		element: () => import('./property-editor-ui-tiptap-statusbar-configuration.element.js'),
+		meta: {
+			label: 'Tiptap Statusbar Configuration',
+			icon: 'icon-autofill',
+			group: 'common',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-statusbar-configuration.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/property-editor-ui-tiptap-statusbar-configuration.element.ts
similarity index 97%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-statusbar-configuration.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/property-editor-ui-tiptap-statusbar-configuration.element.ts
index d7a9be22eff8..59fa60650093 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-statusbar-configuration.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/property-editor-ui-tiptap-statusbar-configuration.element.ts
@@ -1,6 +1,6 @@
-import { UmbTiptapStatusbarConfigurationContext } from '../contexts/tiptap-statusbar-configuration.context.js';
-import type { UmbTiptapStatusbarValue } from '../../../components/types.js';
+import type { UmbTiptapStatusbarValue } from '../../components/types.js';
 import type { UmbTiptapStatusbarViewModel, UmbTiptapStatusbarExtension } from '../types.js';
+import { UmbTiptapStatusbarConfigurationContext } from './tiptap-statusbar-configuration.context.js';
 import { customElement, css, html, property, when, repeat, nothing, state } from '@umbraco-cms/backoffice/external/lit';
 import { debounce } from '@umbraco-cms/backoffice/utils';
 import { UmbLitElement } from '@umbraco-cms/backoffice/lit-element';
@@ -49,9 +49,7 @@ export class UmbPropertyEditorUiTiptapStatusbarConfigurationElement
 			});
 
 			this.observe(this.#context.reload, (reload) => {
-				if (reload) {
-					this.requestUpdate();
-				}
+				if (reload) this.requestUpdate();
 			});
 
 			this.observe(this.#context.statusbar, (statusbar) => {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-statusbar-configuration.context-token.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/tiptap-statusbar-configuration.context-token.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-statusbar-configuration.context-token.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/tiptap-statusbar-configuration.context-token.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-statusbar-configuration.context.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/tiptap-statusbar-configuration.context.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-statusbar-configuration.context.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/tiptap-statusbar-configuration.context.ts
index bc0a680fb8e0..8b3e29cf6eae 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-statusbar-configuration.context.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/statusbar-configuration/tiptap-statusbar-configuration.context.ts
@@ -1,5 +1,5 @@
 import type { UmbTiptapStatusbarExtension, UmbTiptapStatusbarViewModel } from '../types.js';
-import type { UmbTiptapStatusbarValue } from '../../../components/types.js';
+import type { UmbTiptapStatusbarValue } from '../../components/types.js';
 import { UMB_TIPTAP_STATUSBAR_CONFIGURATION_CONTEXT } from './tiptap-statusbar-configuration.context-token.js';
 import { umbExtensionsRegistry } from '@umbraco-cms/backoffice/extension-registry';
 import { UmbArrayState, UmbBooleanState } from '@umbraco-cms/backoffice/observable-api';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/manifests.ts
similarity index 75%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/manifests.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/manifests.ts
index 0dc7c51319a1..9394f778d2e2 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/manifests.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/manifests.ts
@@ -95,37 +95,4 @@ _Drag and drop the available actions onto the statusbar areas._`,
 			},
 		},
 	},
-	{
-		type: 'propertyEditorUi',
-		alias: 'Umb.PropertyEditorUi.Tiptap.ExtensionsConfiguration',
-		name: 'Tiptap Extensions Property Editor UI',
-		element: () => import('./components/property-editor-ui-tiptap-extensions-configuration.element.js'),
-		meta: {
-			label: 'Tiptap Extensions Configuration',
-			icon: 'icon-autofill',
-			group: 'common',
-		},
-	},
-	{
-		type: 'propertyEditorUi',
-		alias: 'Umb.PropertyEditorUi.Tiptap.ToolbarConfiguration',
-		name: 'Tiptap Toolbar Property Editor UI',
-		element: () => import('./components/property-editor-ui-tiptap-toolbar-configuration.element.js'),
-		meta: {
-			label: 'Tiptap Toolbar Configuration',
-			icon: 'icon-autofill',
-			group: 'common',
-		},
-	},
-	{
-		type: 'propertyEditorUi',
-		alias: 'Umb.PropertyEditorUi.Tiptap.StatusbarConfiguration',
-		name: 'Tiptap Statusbar Property Editor UI',
-		element: () => import('./components/property-editor-ui-tiptap-statusbar-configuration.element.js'),
-		meta: {
-			label: 'Tiptap Statusbar Configuration',
-			icon: 'icon-autofill',
-			group: 'common',
-		},
-	},
 ];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.element.ts
similarity index 99%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.element.ts
index 563ffd211779..c979385c79ea 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.element.ts
@@ -69,6 +69,7 @@ export class UmbPropertyEditorUiTiptapElement extends UmbPropertyEditorUiRteElem
 			<umb-input-tiptap
 				style=${styleMap(this._css)}
 				.configuration=${this._config}
+				.label=${this.name}
 				.requiredMessage=${this.mandatoryMessage}
 				.value=${this._markup}
 				?readonly=${this.readonly}
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.stories.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.stories.ts
similarity index 93%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.stories.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.stories.ts
index 5ca150bd66a1..e7309bcd8770 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.stories.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.stories.ts
@@ -30,11 +30,17 @@ const config = new UmbPropertyEditorConfigCollection([
 		alias: 'extensions',
 		value: [
 			'Umb.Tiptap.RichTextEssentials',
+			'Umb.Tiptap.Blockquote',
+			'Umb.Tiptap.Bold',
+			'Umb.Tiptap.BulletList',
 			'Umb.Tiptap.Embed',
 			'Umb.Tiptap.Figure',
+			'Umb.Tiptap.HorizontalRule',
 			'Umb.Tiptap.Image',
+			'Umb.Tiptap.Italic',
 			'Umb.Tiptap.Link',
 			'Umb.Tiptap.MediaUpload',
+			'Umb.Tiptap.OrderedList',
 			'Umb.Tiptap.Subscript',
 			'Umb.Tiptap.Superscript',
 			'Umb.Tiptap.Table',
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.test.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.test.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/property-editor-ui-tiptap.test.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap-rte/property-editor-ui-tiptap.test.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/constants.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/constants.ts
deleted file mode 100644
index be2b430511c3..000000000000
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/constants.ts
+++ /dev/null
@@ -1,2 +0,0 @@
-export { UMB_TIPTAP_STATUSBAR_CONFIGURATION_CONTEXT } from './contexts/tiptap-statusbar-configuration.context-token.js';
-export { UMB_TIPTAP_TOOLBAR_CONFIGURATION_CONTEXT } from './contexts/tiptap-toolbar-configuration.context-token.js';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/manifests.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/manifests.ts
new file mode 100644
index 000000000000..dd26b0056917
--- /dev/null
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/manifests.ts
@@ -0,0 +1,15 @@
+import type { ManifestPropertyEditorUi } from '@umbraco-cms/backoffice/property-editor';
+
+export const manifests: Array<ManifestPropertyEditorUi> = [
+	{
+		type: 'propertyEditorUi',
+		alias: 'Umb.PropertyEditorUi.Tiptap.ToolbarConfiguration',
+		name: 'Tiptap Toolbar Property Editor UI',
+		element: () => import('./property-editor-ui-tiptap-toolbar-configuration.element.js'),
+		meta: {
+			label: 'Tiptap Toolbar Configuration',
+			icon: 'icon-autofill',
+			group: 'common',
+		},
+	},
+];
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-toolbar-configuration.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/property-editor-ui-tiptap-toolbar-configuration.element.ts
similarity index 98%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-toolbar-configuration.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/property-editor-ui-tiptap-toolbar-configuration.element.ts
index 111ea1a4a264..e7612de8f9d0 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/property-editor-ui-tiptap-toolbar-configuration.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/property-editor-ui-tiptap-toolbar-configuration.element.ts
@@ -1,10 +1,10 @@
-import { UmbTiptapToolbarConfigurationContext } from '../contexts/tiptap-toolbar-configuration.context.js';
 import type {
 	UmbTiptapToolbarExtension,
 	UmbTiptapToolbarGroupViewModel,
 	UmbTiptapToolbarRowViewModel,
 } from '../types.js';
-import type { UmbTiptapToolbarValue } from '../../../components/types.js';
+import type { UmbTiptapToolbarValue } from '../../components/types.js';
+import { UmbTiptapToolbarConfigurationContext } from './tiptap-toolbar-configuration.context.js';
 import type { UmbTiptapToolbarGroupConfigurationElement } from './tiptap-toolbar-group-configuration.element.js';
 import { customElement, css, html, property, repeat, state, when, nothing } from '@umbraco-cms/backoffice/external/lit';
 import { debounce } from '@umbraco-cms/backoffice/utils';
@@ -56,9 +56,7 @@ export class UmbPropertyEditorUiTiptapToolbarConfigurationElement
 			});
 
 			this.observe(this.#context.reload, (reload) => {
-				if (reload) {
-					this.requestUpdate();
-				}
+				if (reload) this.requestUpdate();
 			});
 
 			this.observe(this.#context.toolbar, (toolbar) => {
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-toolbar-configuration.context-token.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-configuration.context-token.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-toolbar-configuration.context-token.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-configuration.context-token.ts
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-toolbar-configuration.context.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-configuration.context.ts
similarity index 99%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-toolbar-configuration.context.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-configuration.context.ts
index c758839d3dac..7206a7d33572 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/contexts/tiptap-toolbar-configuration.context.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-configuration.context.ts
@@ -1,4 +1,4 @@
-import type { UmbTiptapToolbarValue } from '../../../components/types.js';
+import type { UmbTiptapToolbarValue } from '../../components/types.js';
 import type {
 	UmbTiptapToolbarExtension,
 	UmbTiptapToolbarGroupViewModel,
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/tiptap-toolbar-group-configuration.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-group-configuration.element.ts
similarity index 97%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/tiptap-toolbar-group-configuration.element.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-group-configuration.element.ts
index 0ec24d6fd60b..ff04c852021d 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/components/tiptap-toolbar-group-configuration.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/toolbar-configuration/tiptap-toolbar-group-configuration.element.ts
@@ -1,5 +1,5 @@
-import { UmbTiptapToolbarConfigurationContext } from '../contexts/tiptap-toolbar-configuration.context.js';
 import type { UmbTiptapToolbarExtension } from '../types.js';
+import { UmbTiptapToolbarConfigurationContext } from './tiptap-toolbar-configuration.context.js';
 import { css, customElement, html, property, repeat, when } from '@umbraco-cms/backoffice/external/lit';
 import { UmbChangeEvent } from '@umbraco-cms/backoffice/event';
 import { UmbLitElement } from '@umbraco-cms/backoffice/lit-element';
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/types.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/types.ts
similarity index 100%
rename from src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/tiptap/types.ts
rename to src/Umbraco.Web.UI.Client/src/packages/tiptap/property-editors/types.ts