diff --git a/test/automation/src/positron/positronEditor.ts b/test/automation/src/positron/positronEditor.ts
index b2adbaea6cc..91a719b84c3 100644
--- a/test/automation/src/positron/positronEditor.ts
+++ b/test/automation/src/positron/positronEditor.ts
@@ -3,7 +3,7 @@
  *  Licensed under the Elastic License 2.0. See LICENSE.txt for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { expect } from '@playwright/test';
+import { expect, FrameLocator, Locator } from '@playwright/test';
 import { Code } from '../code';
 
 // currently a dupe of declaration in ../editor.ts but trying not to modifiy that file
@@ -11,9 +11,21 @@ const EDITOR = (filename: string) => `.monaco-editor[data-uri$="${filename}"]`;
 const CURRENT_LINE = '.view-overlays .current-line';
 const PLAY_BUTTON = '.codicon-play';
 
+const OUTER_FRAME = '.webview';
+const INNER_FRAME = '#active-frame';
 
 export class PositronEditor {
 
+	viewerFrame = this.code.driver.page.frameLocator(OUTER_FRAME).frameLocator(INNER_FRAME);
+
+	getEditorViewerLocator(locator: string,): Locator {
+		return this.viewerFrame.locator(locator);
+	}
+
+	getEditorViewerFrame(): FrameLocator {
+		return this.viewerFrame;
+	}
+
 	constructor(private code: Code) { }
 
 	async pressPlay(): Promise<void> {
@@ -21,7 +33,7 @@ export class PositronEditor {
 
 		// await appearance and disappearance of the toast
 		await expect(this.code.driver.page.locator('.notifications-toasts')).toBeVisible({ timeout: 30000 });
-		await expect(this.code.driver.page.locator('.notifications-toasts')).not.toBeVisible({ timeout: 30000 });
+		await expect(this.code.driver.page.locator('.notifications-toasts')).not.toBeVisible({ timeout: 50000 });
 	}
 
 	async pressToLine(filename: string, lineNumber: number, press: string): Promise<void> {
diff --git a/test/automation/src/positron/positronViewer.ts b/test/automation/src/positron/positronViewer.ts
index 4464ccdd7ad..2a90a16ae53 100644
--- a/test/automation/src/positron/positronViewer.ts
+++ b/test/automation/src/positron/positronViewer.ts
@@ -33,6 +33,15 @@ export class PositronViewer {
 
 	async clearViewer() {
 		await this.code.driver.page.getByRole('tab', { name: 'Viewer' }).locator('a').click();
-		await this.fullApp.getByLabel(/Clear the/).click();
+
+		const clearRegex = /Clear the/;
+
+		if (await this.fullApp.getByLabel(clearRegex).isVisible()) {
+			await this.fullApp.getByLabel(clearRegex).click();
+		}
+	}
+
+	async openViewerToEditor() {
+		await this.code.driver.page.locator('.codicon-go-to-file').click();
 	}
 }
diff --git a/test/smoke/src/areas/positron/apps/python-apps.test.ts b/test/smoke/src/areas/positron/apps/python-apps.test.ts
index 0305667b1e8..bedbac93515 100644
--- a/test/smoke/src/areas/positron/apps/python-apps.test.ts
+++ b/test/smoke/src/areas/positron/apps/python-apps.test.ts
@@ -12,6 +12,8 @@ test.use({
 
 test.describe('Python Applications', { tag: ['@pr'] }, () => {
 	test.afterEach(async function ({ app }) {
+		await app.workbench.quickaccess.runCommand('workbench.action.closeAllEditors');
+
 		await app.workbench.quickaccess.runCommand('workbench.action.terminal.focus');
 		await app.workbench.positronTerminal.sendKeysToTerminal('Control+C');
 		// unreliable on ubuntu:
@@ -26,17 +28,35 @@ test.describe('Python Applications', { tag: ['@pr'] }, () => {
 		await app.workbench.quickaccess.openFile(join(app.workspacePathOrFolder, 'workspaces', 'python_apps', 'dash_example', 'dash_example.py'));
 		await app.workbench.positronEditor.pressPlay();
 		await expect(viewer.getViewerFrame().getByText('Hello World')).toBeVisible({ timeout: 30000 });
+
+		await test.step('Verify app can be opened in editor', async () => {
+			await app.workbench.positronViewer.openViewerToEditor();
+			await app.workbench.positronViewer.clearViewer();
+
+			const editorFrameLocator = app.workbench.positronEditor.getEditorViewerFrame();
+
+			await expect(editorFrameLocator.getByText('Hello World')).toBeVisible({ timeout: 30000 });
+		});
 	});
 
-	// FastAPI is not working as expected on Ubuntu
 	test('Python - Verify Basic FastAPI App [C903306]', async function ({ app, python }) {
 		const viewer = app.workbench.positronViewer;
 
 		await app.workbench.quickaccess.openFile(join(app.workspacePathOrFolder, 'workspaces', 'python_apps', 'fastapi_example', 'fastapi_example.py'));
 		await app.workbench.positronEditor.pressPlay();
 		await expect(viewer.getViewerFrame().getByText('FastAPI')).toBeVisible({ timeout: 30000 });
+
+		await test.step('Verify app can be opened in editor', async () => {
+			await app.workbench.positronViewer.openViewerToEditor();
+			await app.workbench.positronViewer.clearViewer();
+
+			const editorHeaderLocator = app.workbench.positronEditor.getEditorViewerLocator('h2');
+
+			await expect(editorHeaderLocator).toContainText('FastAPI', { timeout: 30000 });
+		});
 	});
 
+	// TODO: update for pop out to editor when issue resolved
 	test.skip('Python - Verify Basic Gradio App [C903307]', {
 		tag: ['@win'],
 		annotation: [{ type: 'issue', description: 'https://github.com/posit-dev/positron/issues/5459' }]
@@ -69,6 +89,20 @@ test.describe('Python Applications', { tag: ['@pr'] }, () => {
 
 			await expect(headerLocator).toBeVisible({ timeout: 30000 });
 		}).toPass({ timeout: 60000 });
+
+		await test.step('Verify app can be opened in editor', async () => {
+			await app.workbench.positronViewer.openViewerToEditor();
+			await app.workbench.positronViewer.clearViewer();
+
+			const editor = app.workbench.positronEditor;
+			const editorFrame = editor.getEditorViewerFrame();
+
+			const headerLocator = app.web
+				? editorFrame.frameLocator('iframe').getByRole('button', { name: 'Deploy' })
+				: editorFrame.getByRole('button', { name: 'Deploy' });
+
+			await expect(headerLocator).toBeVisible({ timeout: 30000 });
+		});
 	});
 
 	test('Python - Verify Basic Flask App [C1013655]', {
@@ -80,7 +114,6 @@ test.describe('Python Applications', { tag: ['@pr'] }, () => {
 		await app.workbench.quickaccess.runCommand('workbench.action.toggleSidebarVisibility');
 		await app.workbench.quickaccess.runCommand('workbench.action.toggleAuxiliaryBar');
 		await app.workbench.positronEditor.pressPlay();
-		await app.workbench.quickaccess.runCommand('workbench.action.toggleAuxiliaryBar');
 		const viewerFrame = viewer.getViewerFrame();
 		const loginLocator = app.web
 			? viewerFrame.frameLocator('iframe').getByText('Log In')
@@ -89,6 +122,21 @@ test.describe('Python Applications', { tag: ['@pr'] }, () => {
 		await expect(async () => {
 			await expect(loginLocator).toBeVisible({ timeout: 30000 });
 		}).toPass({ timeout: 60000 });
+
+		await test.step('Verify app can be opened in editor', async () => {
+			await app.workbench.positronViewer.openViewerToEditor();
+			await app.workbench.positronViewer.clearViewer();
+
+			const editor = app.workbench.positronEditor;
+			const editorFrame = editor.getEditorViewerFrame();
+
+			const loginLocator = app.web
+				? editorFrame.frameLocator('iframe').getByText('Log In')
+				: editorFrame.getByText('Log In');
+
+			await expect(loginLocator).toBeVisible({ timeout: 30000 });
+		});
+
 		await app.workbench.quickaccess.runCommand('workbench.action.toggleSidebarVisibility');
 	});
 });