diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/cascading-menu-popover.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/cascading-menu-popover.element.ts
index 047b6c05891c..8709139f6425 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/cascading-menu-popover.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/components/cascading-menu-popover/cascading-menu-popover.element.ts
@@ -9,6 +9,7 @@ export type UmbCascadingMenuItem = {
 	element?: HTMLElement;
 	separatorAfter?: boolean;
 	style?: string;
+	isActive?: () => boolean | undefined;
 	execute?: () => void;
 };
 
@@ -21,8 +22,12 @@ export class UmbCascadingMenuPopoverElement extends UmbElementMixin(UUIPopoverCo
 		return this.shadowRoot?.querySelector(`#${popoverId}`) as UUIPopoverContainerElement;
 	}
 
-	#onMouseEnter(item: UmbCascadingMenuItem, popoverId: string) {
-		if (!item.items?.length) return;
+	#isMenuActive(items?: UmbCascadingMenuItem[]): boolean {
+		return !!items?.some((item) => item.isActive?.() || this.#isMenuActive(item.items));
+	}
+
+	#onMouseEnter(item: UmbCascadingMenuItem, popoverId?: string) {
+		if (!item.items?.length || !popoverId) return;
 
 		const popover = this.#getPopoverById(popoverId);
 		if (!popover) return;
@@ -33,7 +38,9 @@ export class UmbCascadingMenuPopoverElement extends UmbElementMixin(UUIPopoverCo
 		popover.showPopover();
 	}
 
-	#onMouseLeave(item: UmbCascadingMenuItem, popoverId: string) {
+	#onMouseLeave(item: UmbCascadingMenuItem, popoverId?: string) {
+		if (!popoverId) return;
+
 		const popover = this.#getPopoverById(popoverId);
 		if (!popover) return;
 
@@ -43,12 +50,16 @@ export class UmbCascadingMenuPopoverElement extends UmbElementMixin(UUIPopoverCo
 		popover.hidePopover();
 	}
 
-	#onClick(item: UmbCascadingMenuItem, popoverId: string) {
+	#onClick(item: UmbCascadingMenuItem, popoverId?: string) {
 		item.execute?.();
 
-		setTimeout(() => {
-			this.#onMouseLeave(item, popoverId);
-		}, 100);
+		if (!popoverId) {
+			setTimeout(() => {
+				// eslint-disable-next-line @typescript-eslint/ban-ts-comment
+				// @ts-ignore
+				this.hidePopover();
+			}, 100);
+		}
 	}
 
 	override render() {
@@ -64,14 +75,15 @@ export class UmbCascadingMenuPopoverElement extends UmbElementMixin(UUIPopoverCo
 	}
 
 	#renderItem(item: UmbCascadingMenuItem, index: number) {
-		const popoverId = `item-${index}`;
+		const popoverId = item.items ? `menu-${index}` : undefined;
 
 		const element = item.element;
-		if (element) {
+		if (element && popoverId) {
 			element.setAttribute('popovertarget', popoverId);
 		}
 
 		const label = this.localize.string(item.label);
+		const isActive = item.isActive?.() || this.#isMenuActive(item.items) || false;
 
 		return html`
 			<div
@@ -84,7 +96,9 @@ export class UmbCascadingMenuPopoverElement extends UmbElementMixin(UUIPopoverCo
 						<uui-menu-item
 							class=${item.separatorAfter ? 'separator' : ''}
 							label=${label}
-							popovertarget=${popoverId}
+							popovertarget=${ifDefined(popoverId)}
+							select-mode="highlight"
+							?selected=${isActive}
 							@click-label=${() => this.#onClick(item, popoverId)}>
 							${when(item.icon, (icon) => html`<uui-icon slot="icon" name=${icon}></uui-icon>`)}
 							<div slot="label" class="menu-item">
@@ -94,8 +108,13 @@ export class UmbCascadingMenuPopoverElement extends UmbElementMixin(UUIPopoverCo
 						</uui-menu-item>
 					`,
 				)}
-				<umb-cascading-menu-popover id=${popoverId} placement="right-start" .items=${item.items}>
-				</umb-cascading-menu-popover>
+				${when(
+					popoverId,
+					(popoverId) => html`
+						<umb-cascading-menu-popover id=${popoverId} placement="right-start" .items=${item.items}>
+						</umb-cascading-menu-popover>
+					`,
+				)}
 			</div>
 		`;
 	}
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/components/toolbar/style-menu.tiptap-toolbar-api.ts
index dda2e85f260c..381607675acd 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/components/toolbar/style-menu.tiptap-toolbar-api.ts
@@ -2,14 +2,28 @@ import { UmbTiptapToolbarElementApiBase } from '../../extensions/base.js';
 import type { MetaTiptapToolbarStyleMenuItem } from '../../extensions/types.js';
 import type { ChainedCommands, Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
+type UmbTiptapToolbarStyleMenuCommandType = {
+	type: string;
+	command: (chain: ChainedCommands) => ChainedCommands;
+	isActive?: (editor?: Editor) => boolean | undefined;
+};
+
 export default class UmbTiptapToolbarStyleMenuApi extends UmbTiptapToolbarElementApiBase {
-	#commands: Record<string, { type: string; command: (chain: ChainedCommands) => ChainedCommands }> = {
-		h1: { type: 'heading', command: (chain) => chain.toggleHeading({ level: 1 }) },
-		h2: { type: 'heading', command: (chain) => chain.toggleHeading({ level: 2 }) },
-		h3: { type: 'heading', command: (chain) => chain.toggleHeading({ level: 3 }) },
-		h4: { type: 'heading', command: (chain) => chain.toggleHeading({ level: 4 }) },
-		h5: { type: 'heading', command: (chain) => chain.toggleHeading({ level: 5 }) },
-		h6: { type: 'heading', command: (chain) => chain.toggleHeading({ level: 6 }) },
+	#headingCommand(level: 1 | 2 | 3 | 4 | 5 | 6): UmbTiptapToolbarStyleMenuCommandType {
+		return {
+			type: 'heading',
+			command: (chain) => chain.toggleHeading({ level }),
+			isActive: (editor) => editor?.isActive('heading', { level }),
+		};
+	}
+
+	#commands: Record<string, UmbTiptapToolbarStyleMenuCommandType> = {
+		h1: this.#headingCommand(1),
+		h2: this.#headingCommand(2),
+		h3: this.#headingCommand(3),
+		h4: this.#headingCommand(4),
+		h5: this.#headingCommand(5),
+		h6: this.#headingCommand(6),
 		p: { type: 'paragraph', command: (chain) => chain.setParagraph() },
 		blockquote: { type: 'blockquote', command: (chain) => chain.toggleBlockquote() },
 		code: { type: 'code', command: (chain) => chain.toggleCode() },
@@ -24,6 +38,20 @@ export default class UmbTiptapToolbarStyleMenuApi extends UmbTiptapToolbarElemen
 		ul: { type: 'bulletList', command: (chain) => chain.toggleBulletList() },
 	};
 
+	override isActive(editor?: Editor, item?: MetaTiptapToolbarStyleMenuItem) {
+		if (!editor || !item?.data) return false;
+
+		const { tag, id, class: className } = item.data;
+		const ext = tag ? this.#commands[tag] : null;
+		const attrs = editor?.getAttributes(ext?.type ?? 'paragraph');
+
+		const tagMatch = !tag ? true : ext ? (ext.isActive?.(editor) ?? editor?.isActive(ext.type) ?? false) : false;
+		const idMatch = !id ? true : attrs.id === id;
+		const classMatch = !className ? true : attrs.class?.includes(className) === true;
+
+		return tagMatch && idMatch && classMatch;
+	}
+
 	override execute(editor?: Editor, item?: MetaTiptapToolbarStyleMenuItem) {
 		if (!editor || !item?.data) return;
 		const { tag, id, class: className } = item.data;
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 7f7726eb1040..4ffa6538d43d 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
@@ -99,13 +99,18 @@ export class UmbTiptapToolbarMenuElement extends UmbLitElement {
 			style: item.appearance?.style ?? item.style,
 			separatorAfter: item.separatorAfter,
 			element,
+			isActive: () => this.api?.isActive(this.editor, item),
 			execute: () => this.api?.execute(this.editor, item),
 		};
 	}
 
+	#isMenuActive(items?: UmbCascadingMenuItem[]): boolean {
+		return !!items?.some((item) => item.isActive?.() || this.#isMenuActive(item.items));
+	}
+
 	readonly #onEditorUpdate = () => {
 		if (this.api && this.editor && this.manifest) {
-			this.isActive = this.api.isActive(this.editor);
+			this.isActive = this.api.isActive(this.editor) || this.#isMenuActive(this.#menu) || false;
 		}
 	};
 
@@ -117,8 +122,8 @@ export class UmbTiptapToolbarMenuElement extends UmbLitElement {
 				() => html`
 					<uui-button
 						compact
-						look=${this.isActive ? 'outline' : 'default'}
 						label=${ifDefined(label)}
+						look=${this.isActive ? 'outline' : 'default'}
 						title=${label}
 						popovertarget="popover-menu">
 						${when(
@@ -130,7 +135,11 @@ export class UmbTiptapToolbarMenuElement extends UmbLitElement {
 					</uui-button>
 				`,
 				() => html`
-					<uui-button compact label=${ifDefined(label)} popovertarget="popover-menu">
+					<uui-button
+						compact
+						label=${ifDefined(label)}
+						look=${this.isActive ? 'outline' : 'default'}
+						popovertarget="popover-menu">
 						<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/extensions/table/components/table-toolbar-menu.element.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-toolbar-menu.element.ts
index d57dc1340158..c59e0322659b 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-toolbar-menu.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/table/components/table-toolbar-menu.element.ts
@@ -32,7 +32,7 @@ export class UmbTiptapTableToolbarMenuElement extends UmbTiptapToolbarMenuElemen
 				`,
 			)}
 			${this.renderMenu()}
-			<uui-popover-container id="popover-insert">
+			<uui-popover-container id="popover-insert" style="box-shadow: var(--uui-shadow-depth-3);">
 				<umb-tiptap-table-insert .editor=${this.editor}></umb-tiptap-table-insert>
 			</uui-popover-container>
 		`;
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 6fd0e5bba418..569b913fe667 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
@@ -29,6 +29,11 @@ export class UmbTiptapToolbarTableExtensionApi extends UmbTiptapToolbarElementAp
 		tableProperties: (editor) => this.#tableProperties(editor),
 	};
 
+	override isActive(editor?: Editor, item?: unknown) {
+		if (!item) return super.isActive(editor);
+		return false;
+	}
+
 	async #tableProperties(editor?: Editor) {
 		if (!editor || !editor.isActive('table')) return;
 
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/toolbar/font-family.tiptap-toolbar-api.ts
index 41f698d3f973..4b4c92e03f81 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/toolbar/font-family.tiptap-toolbar-api.ts
@@ -3,6 +3,11 @@ import type { MetaTiptapToolbarMenuItem } from '../types.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarFontFamilyExtensionApi extends UmbTiptapToolbarElementApiBase {
+	override isActive(editor?: Editor, item?: MetaTiptapToolbarMenuItem) {
+		const styles = editor?.getAttributes('span')?.style;
+		return styles?.includes(`font-family: ${item?.data};`) === true;
+	}
+
 	override execute(editor?: Editor, item?: MetaTiptapToolbarMenuItem) {
 		if (!item?.data) return;
 		editor?.chain().focus().toggleSpanStyle(`font-family: ${item.data};`).run();
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/toolbar/font-size.tiptap-toolbar-api.ts
index 3b7f4c5333f7..608807715968 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/toolbar/font-size.tiptap-toolbar-api.ts
@@ -3,6 +3,11 @@ import type { MetaTiptapToolbarMenuItem } from '../types.js';
 import type { Editor } from '@umbraco-cms/backoffice/external/tiptap';
 
 export default class UmbTiptapToolbarFontFamilyExtensionApi extends UmbTiptapToolbarElementApiBase {
+	override isActive(editor?: Editor, item?: MetaTiptapToolbarMenuItem) {
+		const styles = editor?.getAttributes('span')?.style;
+		return styles?.includes(`font-size: ${item?.data};`) === true;
+	}
+
 	override execute(editor?: Editor, item?: MetaTiptapToolbarMenuItem) {
 		if (!item?.data) return;
 		editor?.chain().focus().toggleSpanStyle(`font-size: ${item.data};`).run();
diff --git a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/types.ts b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/types.ts
index 7b2f40033cb5..68d57116931a 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/types.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/tiptap/extensions/types.ts
@@ -54,7 +54,7 @@ export interface UmbTiptapToolbarElementApi extends UmbApi, UmbTiptapExtensionAr
 	/**
 	 * Checks if the toolbar element is active.
 	 */
-	isActive(editor?: Editor): boolean;
+	isActive(editor?: Editor, ...args: Array<unknown>): boolean;
 
 	/**
 	 * Checks if the toolbar element is disabled.