diff --git a/test/automation/src/sql/notebook.ts b/test/automation/src/sql/notebook.ts
index cea041e901..ca20537b11 100644
--- a/test/automation/src/sql/notebook.ts
+++ b/test/automation/src/sql/notebook.ts
@@ -10,6 +10,7 @@ import { Editors } from '../editors';
 import { IElement } from '..';
 
 const winOrCtrl = process.platform === 'win32' ? 'win' : 'ctrl';
+const ctrlOrCmd = process.platform === 'win32' ? 'ctrl' : 'cmd';
 
 export class Notebook {
 
@@ -83,7 +84,7 @@ export class Notebook {
 	public async selectAllTextInEditor(): Promise<void> {
 		const editor = '.notebook-cell.active .monaco-editor';
 		await this.code.waitAndClick(editor);
-		await this.code.dispatchKeybinding('cmd+a');
+		await this.code.dispatchKeybinding(ctrlOrCmd + '+a');
 	}
 
 	private static readonly placeholderSelector = 'div.placeholder-cell-component';
@@ -149,12 +150,9 @@ export class Notebook {
 		await this.code.waitForElementGone(Notebook.doubleClickToEditSelector);
 	}
 
-	async waitForTextCellPreviewContent(text: string, fontType: 'p' | 'h1' | 'h2' | 'h3', textStyle?: 'strong' | 'i' | 'u' | 'mark'): Promise<void> {
-		let textSelector = `${Notebook.textCellPreviewSelector} ${fontType}`;
-		if (textStyle) {
-			textSelector = `${textSelector} ${textStyle}`;
-		}
-		await this.code.waitForElement(textSelector, result => result?.textContent === text);
+	async waitForTextCellPreviewContent(text: string, selector: string): Promise<void> {
+		let textSelector = `${Notebook.textCellPreviewSelector} ${selector}`;
+		await this.code.waitForElement(textSelector, result => !!result?.textContent?.includes(text)); // Use includes to handle whitespace/quote edge cases
 	}
 
 	// Cell Output Actions
@@ -207,7 +205,7 @@ export class Notebook {
 }
 
 export class TextCellToolbar {
-	private static readonly textCellToolbar = 'text-cell-component markdown-toolbar-component ul.actions-container';
+	private static readonly textCellToolbar = 'text-cell-component markdown-toolbar-component ul.actions-container li.action-item';
 
 	constructor(private code: Code) { }
 
@@ -220,7 +218,7 @@ export class TextCellToolbar {
 	}
 
 	public async italicizeSelectedText(): Promise<void> {
-		await this.clickToolbarButton('Italics');
+		await this.clickToolbarButton('Italic');
 	}
 
 	public async underlineSelectedText(): Promise<void> {
@@ -232,7 +230,7 @@ export class TextCellToolbar {
 	}
 
 	public async codifySelectedText(): Promise<void> {
-		await this.clickToolbarButton('Code');
+		await this.clickToolbarButton('Insert code');
 	}
 
 	public async insertLink(): Promise<void> {
@@ -240,11 +238,11 @@ export class TextCellToolbar {
 	}
 
 	public async insertList(): Promise<void> {
-		await this.clickToolbarButton('List');
+		await this.clickToolbarButton('Insert list');
 	}
 
 	public async insertOrderedList(): Promise<void> {
-		await this.clickToolbarButton('Ordered list');
+		await this.clickToolbarButton('Insert ordered list');
 	}
 
 	public async changeSelectedTextSize(): Promise<void> {
diff --git a/test/smoke/src/sql/areas/notebook/notebook.test.ts b/test/smoke/src/sql/areas/notebook/notebook.test.ts
index 0660a2430c..9130fa57e4 100644
--- a/test/smoke/src/sql/areas/notebook/notebook.test.ts
+++ b/test/smoke/src/sql/areas/notebook/notebook.test.ts
@@ -31,7 +31,7 @@ export function setup(opts: minimist.ParsedArgs) {
 			await app.workbench.sqlNotebook.selectAllTextInEditor();
 			await app.workbench.sqlNotebook.textCellToolbar.boldSelectedText();
 			await app.code.dispatchKeybinding('escape');
-			await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'p', 'strong');
+			await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'p strong');
 		});
 
 		it('can perform basic code cell functionality', async function () {
@@ -145,6 +145,74 @@ export function setup(opts: minimist.ParsedArgs) {
 			});
 		});
 
+		describe('Cell Toolbar Actions', function () {
+			const sampleText: string = 'Test Text';
+			async function createCellAndSelectAllText(app: Application): Promise<void> {
+				await app.workbench.sqlNotebook.newUntitledNotebook();
+				await app.workbench.sqlNotebook.addCellFromPlaceholder('Markdown');
+				await app.workbench.sqlNotebook.waitForPlaceholderGone();
+				await app.workbench.sqlNotebook.textCellToolbar.changeTextCellView('Split View');
+				await app.workbench.sqlNotebook.waitForTypeInEditor(sampleText);
+				await app.workbench.sqlNotebook.selectAllTextInEditor();
+			}
+
+			it('can bold selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.boldSelectedText();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'p strong');
+			});
+
+			it('can italicize selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.italicizeSelectedText();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'p em');
+			});
+
+			it('can underline selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.underlineSelectedText();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'p u');
+			});
+
+			it('can highlight selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.highlightSelectedText();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'p mark');
+			});
+
+			it('can codify selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.codifySelectedText();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'pre code');
+			});
+
+			it('can bullet selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.insertList();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'ul li');
+			});
+
+			it('can number selected text', async function () {
+				const app = this.app as Application;
+				await createCellAndSelectAllText(app);
+				await app.workbench.sqlNotebook.textCellToolbar.insertOrderedList();
+				await app.code.dispatchKeybinding('escape');
+				await app.workbench.sqlNotebook.waitForTextCellPreviewContent(sampleText, 'ol li');
+			});
+		});
+
 		describe('markdown', function () {
 			it('can create http link from markdown', async function () {
 				const app = this.app as Application;