diff --git a/src/Umbraco.Web.UI.Client/src/packages/core/components/input-markdown-editor/input-markdown.element.ts b/src/Umbraco.Web.UI.Client/src/packages/core/components/input-markdown-editor/input-markdown.element.ts
index e9202df63b..23d31e1088 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/core/components/input-markdown-editor/input-markdown.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/core/components/input-markdown-editor/input-markdown.element.ts
@@ -1,8 +1,15 @@
-import { UmbCodeEditorElement, loadCodeEditor } from '@umbraco-cms/backoffice/code-editor';
-import { css, html, customElement, query, property } from '@umbraco-cms/backoffice/external/lit';
+import { KeyCode, KeyMod } from 'monaco-editor';
+import { UmbCodeEditorController, UmbCodeEditorElement, loadCodeEditor } from '@umbraco-cms/backoffice/code-editor';
+import { css, html, customElement, query, property, state } from '@umbraco-cms/backoffice/external/lit';
 import { FormControlMixin } from '@umbraco-cms/backoffice/external/uui';
 import { UmbBooleanState } from '@umbraco-cms/backoffice/observable-api';
 import { UmbLitElement } from '@umbraco-cms/internal/lit-element';
+import {
+	UMB_LINK_PICKER_MODAL,
+	UMB_MEDIA_TREE_PICKER_MODAL,
+	UMB_MODAL_MANAGER_CONTEXT_TOKEN,
+	UmbModalManagerContext,
+} from '@umbraco-cms/backoffice/modal';
 
 /**
  * @element umb-input-markdown
@@ -12,40 +19,514 @@ import { UmbLitElement } from '@umbraco-cms/internal/lit-element';
 @customElement('umb-input-markdown')
 export class UmbInputMarkdownElement extends FormControlMixin(UmbLitElement) {
 	protected getFormElement() {
-		return undefined;
+		return this._codeEditor;
 	}
 
 	@property({ type: Boolean })
 	preview?: boolean;
 
 	#isCodeEditorReady = new UmbBooleanState(false);
-	isCodeEditorReady = this.#isCodeEditorReady.asObservable();
+	#editor?: UmbCodeEditorController;
 
 	@query('umb-code-editor')
 	_codeEditor?: UmbCodeEditorElement;
 
+	private _modalContext?: UmbModalManagerContext;
+
 	constructor() {
 		super();
 		this.#loadCodeEditor();
+		this.consumeContext(UMB_MODAL_MANAGER_CONTEXT_TOKEN, (instance) => {
+			this._modalContext = instance;
+		});
 	}
 
 	async #loadCodeEditor() {
 		try {
 			await loadCodeEditor();
-			this._codeEditor?.editor?.updateOptions({
+			this.#isCodeEditorReady.next(true);
+
+			this.#editor = this._codeEditor?.editor;
+
+			this.#editor?.updateOptions({
 				lineNumbers: false,
 				minimap: false,
 				folding: false,
 			});
-			this.#isCodeEditorReady.next(true);
+			this.#loadActions();
 		} catch (error) {
 			console.error(error);
 		}
 	}
 
+	async #loadActions() {
+		// TODO: Find a way to have "double" keybindings (ctrl+m+ctrl+c for `code`, rather than simple ctrl+c as its taken by OS to copy things)
+		// Going with the keybindings of a Markdown Shortcut plugin https://marketplace.visualstudio.com/items?itemName=robole.markdown-shortcuts#shortcuts or perhaps there are keybindings that would make more sense.
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Heading H1',
+			id: 'h1',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.Digit1],
+			run: () => this._insertAtCurrentLine('#'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Heading H2',
+			id: 'h2',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.Digit2],
+			run: () => this._insertAtCurrentLine('##'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Heading H3',
+			id: 'h3',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.Digit3],
+			run: () => this._insertAtCurrentLine('###'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Heading H4',
+			id: 'h4',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.Digit4],
+			run: () => this._insertAtCurrentLine('####'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Heading H5',
+			id: 'h5',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.Digit5],
+			run: () => this._insertAtCurrentLine('#####'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Heading H6',
+			id: 'h6',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.Digit6],
+			run: () => this._insertAtCurrentLine('######'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Bold Text',
+			id: 'b',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.KeyB],
+			run: () => this._insertBetweenSelection('**', '**', 'Your Bold Text'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Italic Text',
+			id: 'i',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.KeyI],
+			run: () => this._insertBetweenSelection('*', '*', 'Your Italic Text'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Quote',
+			id: 'q',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.KeyQ],
+			run: () => this._insertQuote(),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Ordered List',
+			id: 'ol',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.KeyO],
+			run: () => this._insertAtCurrentLine('1. '),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Unordered List',
+			id: 'ul',
+			keybindings: [KeyMod.CtrlCmd | KeyCode.KeyU],
+			run: () => this._insertAtCurrentLine('- '),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Code',
+			id: 'code',
+			//keybindings: [KeyMod.CtrlCmd | KeyCode.KeyM | KeyMod.CtrlCmd | KeyCode.KeyC],
+			run: () => this._insertBetweenSelection('`', '`', 'Code'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Fenced Code',
+			id: 'fenced-code',
+			//keybindings: [KeyMod.CtrlCmd | KeyCode.KeyM | KeyMod.CtrlCmd | KeyCode.KeyF],
+			run: () => this._insertBetweenSelection('```', '```', 'Code'),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Line',
+			id: 'line',
+			//keybindings: [KeyMod.CtrlCmd | KeyCode.KeyM | KeyMod.CtrlCmd | KeyCode.KeyC],
+			run: () => this._insertLine(),
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Link',
+			id: 'link',
+			//keybindings: [KeyMod.CtrlCmd | KeyCode.KeyM | KeyMod.CtrlCmd | KeyCode.KeyC],
+			run: () => this._insertLink(),
+			// TODO: Open in modal
+		});
+		this.#editor?.monacoEditor?.addAction({
+			label: 'Add Image',
+			id: 'image',
+			//keybindings: [KeyMod.CtrlCmd | KeyCode.KeyM | KeyMod.CtrlCmd | KeyCode.KeyC],
+			run: () => this._insertMedia(),
+			// TODO: Open in modal
+		});
+	}
+
+	private _focusEditor(): void {
+		// If we press one of the action buttons manually (which is outside the editor), we need to focus the editor again.
+		this.#editor?.monacoEditor?.focus();
+	}
+
+	private _insertLink() {
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		const selectedValue = this.#editor?.getValueInRange(selection);
+
+		this._focusEditor(); // Focus before opening modal
+		const modalContext = this._modalContext?.open(UMB_LINK_PICKER_MODAL, {
+			index: null,
+			link: { name: selectedValue },
+			config: {},
+		});
+
+		modalContext
+			?.onSubmit()
+			.then((data) => {
+				const name = this.localize.term('general_name');
+				const url = this.localize.term('general_url');
+
+				this.#editor?.monacoEditor?.executeEdits('', [
+					{ range: selection, text: `[${data.link.name || name}](${data.link.url || url})` },
+				]);
+
+				if (!data.link.name) {
+					this.#editor?.select({
+						startColumn: selection.startColumn + 1,
+						endColumn: selection.startColumn + 1 + name.length,
+						endLineNumber: selection.startLineNumber,
+						startLineNumber: selection.startLineNumber,
+					});
+				} else if (!data.link.url) {
+					this.#editor?.select({
+						startColumn: selection.startColumn + 3 + data.link.name.length,
+						endColumn: selection.startColumn + 3 + data.link.name.length + url.length,
+						endLineNumber: selection.startLineNumber,
+						startLineNumber: selection.startLineNumber,
+					});
+				}
+			})
+			.catch(() => undefined)
+			.finally(() => this._focusEditor());
+	}
+
+	private _insertMedia() {
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		const alt = this.#editor?.getValueInRange(selection);
+
+		this._focusEditor(); // Focus before opening modal
+		const modalContext = this._modalContext?.open(UMB_MEDIA_TREE_PICKER_MODAL, {});
+
+		modalContext
+			?.onSubmit()
+			.then((data) => {
+				const imgUrl = data.selection[0];
+				this.#editor?.monacoEditor?.executeEdits('', [
+					//TODO: media url
+					{ range: selection, text: `[${alt || 'alt text'}](TODO: id-${imgUrl || this.localize.term('general_url')})` },
+				]);
+
+				if (!alt?.length) {
+					this.#editor?.select({
+						startColumn: selection.startColumn + 1,
+						endColumn: selection.startColumn + 9,
+						endLineNumber: selection.startLineNumber,
+						startLineNumber: selection.startLineNumber,
+					});
+				}
+			})
+			.catch(() => undefined)
+			.finally(() => this._focusEditor());
+	}
+
+	private _insertLine() {
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		const endColumn = this.#editor?.monacoModel?.getLineMaxColumn(selection.endLineNumber) ?? 1;
+
+		if (endColumn === 1) {
+			this.#editor?.insertAtPosition('---\n', {
+				lineNumber: selection.endLineNumber,
+				column: 1,
+			});
+		} else {
+			this.#editor?.insertAtPosition('\n---\n', {
+				lineNumber: selection.endLineNumber,
+				column: endColumn,
+			});
+		}
+		this._focusEditor();
+	}
+
+	private _insertBetweenSelection(startValue: string, endValue: string, placeholder?: string) {
+		this._focusEditor();
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		const selectedValue = this.#editor?.getValueInRange({
+			startLineNumber: selection.startLineNumber,
+			endLineNumber: selection.endLineNumber,
+			startColumn: selection.startColumn - startValue.length,
+			endColumn: selection.endColumn + endValue.length,
+		});
+
+		if (
+			selectedValue?.startsWith(startValue) &&
+			selectedValue.endsWith(endValue) &&
+			selectedValue.length > startValue.length + endValue.length
+		) {
+			//Cancel previous insert
+			this.#editor?.select({ ...selection, startColumn: selection.startColumn + startValue.length });
+			this.#editor?.monacoEditor?.executeEdits('', [
+				{
+					range: {
+						startColumn: selection.startColumn - startValue.length,
+						startLineNumber: selection.startLineNumber,
+						endColumn: selection.startColumn,
+						endLineNumber: selection.startLineNumber,
+					},
+					text: '',
+				},
+				{
+					range: {
+						startColumn: selection.endColumn + startValue.length,
+						startLineNumber: selection.startLineNumber,
+						endColumn: selection.endColumn,
+						endLineNumber: selection.startLineNumber,
+					},
+					text: '',
+				},
+			]);
+		} else {
+			// Insert
+			this.#editor?.insertAtPosition(startValue, {
+				lineNumber: selection.startLineNumber,
+				column: selection.startColumn,
+			});
+			this.#editor?.insertAtPosition(endValue, {
+				lineNumber: selection.endLineNumber,
+				column: selection.endColumn + startValue.length,
+			});
+
+			this.#editor?.select({
+				startLineNumber: selection.startLineNumber,
+				endLineNumber: selection.endLineNumber,
+				startColumn: selection.startColumn + startValue.length,
+				endColumn: selection.endColumn + startValue.length,
+			});
+		}
+
+		// if no text were selected when action fired
+		if (selection.startColumn === selection.endColumn && selection.startLineNumber === selection.endLineNumber) {
+			if (placeholder) {
+				this.#editor?.insertAtPosition(placeholder, {
+					lineNumber: selection.startLineNumber,
+					column: selection.startColumn + startValue.length,
+				});
+			}
+
+			this.#editor?.select({
+				startLineNumber: selection.startLineNumber,
+				endLineNumber: selection.endLineNumber,
+				startColumn: selection.startColumn + startValue.length,
+				endColumn: selection.startColumn + startValue.length + (placeholder?.length ?? 0),
+			});
+		}
+	}
+
+	private _insertAtCurrentLine(value: string) {
+		this._focusEditor();
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		const previousLineValue = this.#editor?.getValueInRange({
+			...selection,
+			startLineNumber: selection.startLineNumber - 1,
+		});
+		const lineValue = this.#editor?.getValueInRange({ ...selection, startColumn: 1 });
+
+		// Regex: check if the line starts with a positive number followed by dot and a space
+		if (lineValue?.startsWith(value) || lineValue?.match(/^[1-9]\d*\.\s.*/)) {
+			// Cancel previous insert
+			this.#editor?.monacoEditor?.executeEdits('', [
+				{
+					range: {
+						startColumn: 1,
+						startLineNumber: selection.startLineNumber,
+						endColumn: 1 + value.length,
+						endLineNumber: selection.startLineNumber,
+					},
+					text: '',
+				},
+			]);
+		} else if (value.match(/^[1-9]\d*\.\s.*/) && previousLineValue?.match(/^[1-9]\d*\.\s.*/)) {
+			// Check if the PREVIOUS line starts with a positive number followed by dot and a space. If yes, get that number.
+			const previousNumber = parseInt(previousLineValue, 10);
+			this.#editor?.insertAtPosition(`${previousNumber + 1}. `, {
+				lineNumber: selection.startLineNumber,
+				column: 1,
+			});
+		} else {
+			// Insert
+			this.#editor?.insertAtPosition(value, {
+				lineNumber: selection.startLineNumber,
+				column: 1,
+			});
+		}
+	}
+
+	private _insertQuote() {
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		let index = selection.startLineNumber;
+		for (index; index <= selection.endLineNumber; index++) {
+			const line = this.#editor?.getValueInRange({
+				startLineNumber: index,
+				endLineNumber: index,
+				startColumn: 1,
+				endColumn: 3,
+			});
+			if (!line?.startsWith('> ')) {
+				this.#editor?.insertAtPosition('> ', {
+					lineNumber: index,
+					column: 1,
+				});
+			}
+		}
+		this._focusEditor();
+	}
+
+	private _renderBasicActions() {
+		return html`<div>
+				<uui-button
+					compact
+					look="secondary"
+					label="Heading"
+					title="Heading"
+					@click=${() => this.#editor?.monacoEditor?.getAction('h1')?.run()}>
+					H
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Bold"
+					title="Bold"
+					@click=${() => this.#editor?.monacoEditor?.getAction('b')?.run()}>
+					B
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Italic"
+					title="Italic"
+					@click=${() => this.#editor?.monacoEditor?.getAction('i')?.run()}>
+					I
+				</uui-button>
+			</div>
+			<div>
+				<uui-button
+					compact
+					look="secondary"
+					label="Quote"
+					title="Quote"
+					@click=${() => this.#editor?.monacoEditor?.getAction('q')?.run()}>
+					<uui-icon name="umb:quote"></uui-icon>
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Ordered List"
+					title="Ordered List"
+					@click=${() => this.#editor?.monacoEditor?.getAction('ol')?.run()}>
+					<uui-icon name="umb:ordered-list"></uui-icon>
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Unordered List"
+					title="Unordered List"
+					@click=${() => this.#editor?.monacoEditor?.getAction('ul')?.run()}>
+					<uui-icon name="umb:bulleted-list"></uui-icon>
+				</uui-button>
+			</div>
+			<div>
+				<uui-button
+					compact
+					look="secondary"
+					label="Fenced Code"
+					title="Fenced Code"
+					@click=${() => this.#editor?.monacoEditor?.getAction('fenced-code')?.run()}>
+					<uui-icon name="umb:code"></uui-icon>
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Line"
+					title="Line"
+					@click=${() => this.#editor?.monacoEditor?.getAction('line')?.run()}>
+					<uui-icon name="umb:width"></uui-icon>
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Link"
+					title="Link"
+					@click=${() => this.#editor?.monacoEditor?.getAction('link')?.run()}>
+					<uui-icon name="umb:link"></uui-icon>
+				</uui-button>
+				<uui-button
+					compact
+					look="secondary"
+					label="Image"
+					title="Image"
+					@click=${() => this.#editor?.monacoEditor?.getAction('image')?.run()}>
+					<uui-icon name="umb:picture"></uui-icon>
+				</uui-button>
+			</div>
+			<div>
+				<uui-button
+					compact
+					label="Press F1 for all actions"
+					title="Press F1 for all actions"
+					@click=${() => {
+						this._focusEditor();
+						this.#editor?.monacoEditor?.trigger('', 'editor.action.quickCommand', '');
+					}}>
+					<uui-key>F1</uui-key>
+				</uui-button>
+			</div>`;
+	}
+
+	onKeyPress(e: KeyboardEvent) {
+		if (e.key !== 'Enter') return;
+		//TODO: Tab does not seem to trigger keyboard events. We need to make some logic for ordered and unordered lists when tab is being used.
+
+		const selection = this.#editor?.getSelections()[0];
+		if (!selection) return;
+
+		const lineValue = this.#editor?.getValueInRange({ ...selection, startColumn: 1 }).trimStart();
+		if (!lineValue) return;
+
+		if (lineValue.startsWith('- ') && lineValue.length > 2) {
+			requestAnimationFrame(() => this.#editor?.insert('- '));
+		} else if (lineValue.match(/^[1-9]\d*\.\s.*/) && lineValue.length > 3) {
+			const previousNumber = parseInt(lineValue, 10);
+			requestAnimationFrame(() => this.#editor?.insert(`${previousNumber + 1}. `));
+		}
+	}
+
 	render() {
-		return html` <div id="actions"></div>
-			<umb-code-editor language="markdown" .code=${this.value as string}></umb-code-editor>
+		//TODO: Why is the theme dark in Backoffice, but light in Storybook?
+		return html` <div id="actions">${this._renderBasicActions()}</div>
+			<umb-code-editor
+				language="markdown"
+				.code=${this.value as string}
+				@keypress=${this.onKeyPress}
+				theme="umb-light"></umb-code-editor>
 			${this.renderPreview()}`;
 	}
 
@@ -63,6 +544,16 @@ export class UmbInputMarkdownElement extends FormControlMixin(UmbLitElement) {
 			#actions {
 				background-color: var(--uui-color-background-alt);
 				display: flex;
+				gap: var(--uui-size-6);
+			}
+
+			#actions div {
+				display: flex;
+				gap: var(--uui-size-1);
+			}
+
+			#actions div:last-child {
+				margin-left: auto;
 			}
 
 			umb-code-editor {
@@ -70,6 +561,10 @@ export class UmbInputMarkdownElement extends FormControlMixin(UmbLitElement) {
 				border-radius: var(--uui-border-radius);
 				border: 1px solid var(--uui-color-divider-emphasis);
 			}
+
+			uui-button {
+				width: 50px;
+			}
 		`,
 	];
 }
diff --git a/src/Umbraco.Web.UI.Client/src/packages/core/modal/common/link-picker/link-picker-modal.element.ts b/src/Umbraco.Web.UI.Client/src/packages/core/modal/common/link-picker/link-picker-modal.element.ts
index aece02e1a1..df38f1f184 100644
--- a/src/Umbraco.Web.UI.Client/src/packages/core/modal/common/link-picker/link-picker-modal.element.ts
+++ b/src/Umbraco.Web.UI.Client/src/packages/core/modal/common/link-picker/link-picker-modal.element.ts
@@ -153,6 +153,7 @@ export class UmbLinkPickerModalElement extends UmbModalBaseElement<UmbLinkPicker
 		return html`<uui-label for="search-input">Link to page</uui-label>
 			<uui-input id="search-input" placeholder="Type to search" label="Type to search"></uui-input>
 			<umb-tree
+				?multiple=${false}
 				alias="Umb.Tree.Documents"
 				@selected=${(event: CustomEvent) => this._handleSelectionChange(event, 'document')}
 				.selection=${[this._selectedKey ?? '']}
@@ -163,6 +164,7 @@ export class UmbLinkPickerModalElement extends UmbModalBaseElement<UmbLinkPicker
 			<uui-label>Link to media</uui-label>
 
 			<umb-tree
+				?multiple=${false}
 				alias="Umb.Tree.Media"
 				@selected=${(event: CustomEvent) => this._handleSelectionChange(event, 'media')}
 				.selection=${[this._selectedKey ?? '']}