diff --git a/test/automation/src/index.ts b/test/automation/src/index.ts
index fbbd96b1e88..5560b4386e8 100644
--- a/test/automation/src/index.ts
+++ b/test/automation/src/index.ts
@@ -52,5 +52,7 @@ export * from './positron/positronEditor';
 export * from './positron/positronTestExplorer';
 export * from './positron/positronExplorer';
 export * from './positron/utils/positronAWSUtils';
+export * from './positron/positronQuickaccess';
+export * from './positron/positronOutline';
 // --- End Positron ---
 export { getDevElectronPath, getBuildElectronPath, getBuildVersion } from './electron';
diff --git a/test/automation/src/positron/positronDataExplorer.ts b/test/automation/src/positron/positronDataExplorer.ts
index 2a8d056daf7..8e3f9e09678 100644
--- a/test/automation/src/positron/positronDataExplorer.ts
+++ b/test/automation/src/positron/positronDataExplorer.ts
@@ -56,7 +56,7 @@ export class PositronDataExplorer {
 
 		// unreliable:
 		//await this.code.waitForElement(IDLE_STATUS);
-		await this.code.driver.getLocator(IDLE_STATUS).waitFor({ state: 'visible', timeout: 30000 });
+		await this.code.driver.getLocator(IDLE_STATUS).waitFor({ state: 'visible', timeout: 60000 });
 
 		// we have seen intermittent failures where the data explorer is not fully loaded
 		// even though the status bar is idle. This wait is to ensure the data explorer is fully loaded
diff --git a/test/automation/src/positron/positronOutline.ts b/test/automation/src/positron/positronOutline.ts
new file mode 100644
index 00000000000..0ae5c8b19ca
--- /dev/null
+++ b/test/automation/src/positron/positronOutline.ts
@@ -0,0 +1,57 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (C) 2024 Posit Software, PBC. All rights reserved.
+ *  Licensed under the Elastic License 2.0. See LICENSE.txt for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+
+import { fail } from 'assert';
+import { Code } from '../code';
+import { QuickAccess } from '../quickaccess';
+
+const HORIZONTAL_SASH = '.explorer-viewlet .monaco-sash.horizontal';
+const FOCUS_OUTLINE_COMMAND = 'outline.focus';
+const OUTLINE_ELEMENT = '.outline-element';
+
+/*
+ *  Reuseable Positron outline functionality for tests to leverage.
+ */
+export class PositronOutline {
+
+	constructor(private code: Code, private quickaccess: QuickAccess) { }
+
+	async getOutlineData(): Promise<string[]> {
+
+		await this.quickaccess.runCommand(FOCUS_OUTLINE_COMMAND);
+
+		const sashLocator = this.code.driver.page.locator(HORIZONTAL_SASH).nth(1);
+		const sashBoundingBox = await sashLocator.boundingBox();
+
+		if (sashBoundingBox) {
+
+			await this.code.driver.clickAndDrag({
+				from: {
+					x: sashBoundingBox.x + 10,
+					y: sashBoundingBox.y
+				},
+				to: {
+					x: sashBoundingBox.x + 10,
+					y: sashBoundingBox.y - 150
+				}
+			});
+		} else {
+			fail('Bounding box not found');
+		}
+
+		const outllineElements = await this.code.waitForElements(OUTLINE_ELEMENT, false);
+
+		const outlineData: string[] = [];
+		for (let i = 0; i < outllineElements.length; i++) {
+			const element = outllineElements[i];
+			const text = element.textContent;
+			outlineData.push(text);
+		}
+
+		return outlineData;
+	}
+
+}
diff --git a/test/automation/src/workbench.ts b/test/automation/src/workbench.ts
index ccb832acf50..10684dbfb35 100644
--- a/test/automation/src/workbench.ts
+++ b/test/automation/src/workbench.ts
@@ -45,6 +45,7 @@ import { PositronViewer } from './positron/positronViewer';
 import { PositronEditor } from './positron/positronEditor';
 import { PositronTestExplorer } from './positron/positronTestExplorer';
 import { PositronQuickAccess } from './positron/positronQuickaccess';
+import { PositronOutline } from './positron/positronOutline';
 // --- End Positron ---
 
 export interface Commands {
@@ -94,6 +95,7 @@ export class Workbench {
 	readonly positronEditor: PositronEditor;
 	readonly positronTestExplorer: PositronTestExplorer;
 	readonly positronQuickaccess: PositronQuickAccess;
+	readonly positronOutline: PositronOutline;
 	// --- End Positron ---
 
 	constructor(code: Code) {
@@ -138,6 +140,7 @@ export class Workbench {
 		this.positronEditor = new PositronEditor(code);
 		this.positronTestExplorer = new PositronTestExplorer(code);
 		this.positronQuickaccess = new PositronQuickAccess(this.quickinput, this.quickaccess);
+		this.positronOutline = new PositronOutline(code, this.quickaccess);
 		// --- End Positron ---
 	}
 }
diff --git a/test/smoke/src/areas/positron/outline/outline.test.ts b/test/smoke/src/areas/positron/outline/outline.test.ts
new file mode 100644
index 00000000000..51b66ae33b3
--- /dev/null
+++ b/test/smoke/src/areas/positron/outline/outline.test.ts
@@ -0,0 +1,70 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (C) 2024 Posit Software, PBC. All rights reserved.
+ *  Licensed under the Elastic License 2.0. See LICENSE.txt for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+
+import { join } from 'path';
+import { Application, PositronPythonFixtures, PositronRFixtures } from '../../../../../automation';
+import { setupAndStartApp } from '../../../test-runner/test-hooks';
+
+
+describe('Outline #web #win', () => {
+	setupAndStartApp();
+
+	describe('Outline Test - Python', () => {
+		before(async function () {
+			await PositronPythonFixtures.SetupFixtures(this.app as Application);
+		});
+
+		it('Python - Verify Outline Contents [C956870]', async function () {
+			const app = this.app as Application;
+			await app.workbench.quickaccess.openFile(join(app.workspacePathOrFolder, 'workspaces', 'chinook-db-py', 'chinook-sqlite.py'));
+
+			const outlineData = await app.workbench.positronOutline.getOutlineData();
+
+			const expected = [
+				'data_file_pathdata_file_path = os.path.join(os.getcwd(), \'data-files\', \'chinook\', \'chinook.db\')',
+				'connconn = sqlite3.connect(data_file_path)',
+				'curcur = conn.cursor()',
+				'rowsrows = cur.fetchall()',
+				'dfdf = pd.DataFrame(rows)'
+			];
+
+			const missingFromUI = expected.filter(item => !outlineData.includes(item));
+
+			if (missingFromUI.length > 0) {
+				console.log(`Missing from UI: ${missingFromUI}`);
+			}
+		});
+	});
+
+
+
+	describe('Outline Test - R', () => {
+		before(async function () {
+			await PositronRFixtures.SetupFixtures(this.app as Application);
+		});
+
+		it('R - Verify Outline Contents [C956871]', async function () {
+			const app = this.app as Application;
+			await app.workbench.quickaccess.openFile(join(app.workspacePathOrFolder, 'workspaces', 'chinook-db-r', 'chinook-sqlite.r'));
+
+			const outlineData = await app.workbench.positronOutline.getOutlineData();
+
+			const expected = [
+				'con',
+				'albums',
+				'df',
+			];
+
+			const missingFromUI = expected.filter(item => !outlineData.includes(item));
+
+			if (missingFromUI.length > 0) {
+				console.log(`Missing from UI: ${missingFromUI}`);
+			}
+		});
+	});
+});
+
+