diff --git a/package.json b/package.json
index 3da9c013cbf..38d54b2fa0e 100644
--- a/package.json
+++ b/package.json
@@ -30,7 +30,7 @@
         "testE2E": "npm run testE2E -w packages/ --if-present",
         "test:ui:prepare": "./node_modules/.bin/extest get-vscode -s ~/.vscode-test-resources -n && extest get-chromedriver -s ~/.vscode-test-resources -n",
         "test:ui:install": "cd packages/amazonq && npm run package 2>&1 | grep -o 'VSIX Version: [^ ]*' | cut -d' ' -f3 | xargs -I{} bash -c 'cd ../../ && ./node_modules/.bin/extest install-vsix -f amazon-q-vscode-{}.vsix -e packages/amazonq/test/e2e_new/amazonq/resources -s ~/.vscode-test-resources'",
-        "test:ui:run": "npm run testCompile && ./node_modules/.bin/extest run-tests -s ~/.vscode-test-resources -e packages/amazonq/test/e2e_new/amazonq/resources packages/amazonq/dist/test/e2e_new/amazonq/tests/*.js",
+        "test:ui:run": "npm run testCompile && ./node_modules/.bin/extest run-tests -s ~/.vscode-test-resources -e packages/amazonq/test/e2e_new/amazonq/resources packages/amazonq/dist/test/e2e_new/amazonq/tests/*.test.js",
         "test:ui": "npm run test:ui:prepare && npm run test:ui:install && npm run test:ui:run",
         "testInteg": "npm run testInteg -w packages/ --if-present",
         "package": "npm run package -w packages/toolkit -w packages/amazonq",
diff --git a/packages/amazonq/test/e2e_new/amazonq/tests/inline.test.ts b/packages/amazonq/test/e2e_new/amazonq/tests/inline.test.ts
index 6c8d975206d..0433b67afc0 100644
--- a/packages/amazonq/test/e2e_new/amazonq/tests/inline.test.ts
+++ b/packages/amazonq/test/e2e_new/amazonq/tests/inline.test.ts
@@ -5,7 +5,7 @@
 import '../utils/setup'
 import { Workbench, EditorView, InputBox, TextEditor, WebviewView, Key } from 'vscode-extension-tester'
 import { testContext } from '../utils/testContext'
-import { pressKey, createNewTextFile, writeToTextEditor } from '../utils/generalUtils'
+import { createNewTextFile, writeToTextEditor, sleep } from '../utils/generalUtils'
 import assert from 'assert'
 
 describe('Amazon Q Inline Completion / Chat Functionality', function () {
@@ -20,25 +20,31 @@ describe('Amazon Q Inline Completion / Chat Functionality', function () {
         webviewView = testContext.webviewView
         await webviewView.switchBack()
         workbench = testContext.workbench
-
         editorView = new EditorView()
         testContext.editorView = editorView
-
         textEditor = await createNewTextFile(workbench, editorView)
     })
-
-    it('Inline Test', async () => {
-        await writeToTextEditor(textEditor, 'Select Me')
+    after(async function () {
+        // Switch back to Webview Iframe when dealing with external webviews from Amazon Q.
+        await editorView.closeAllEditors()
+        await webviewView.switchToFrame()
+    })
+    it('Inline Test Shortcut', async () => {
+        await writeToTextEditor(textEditor, 'def factorial(n):')
         const text = await textEditor.getText()
-        assert.equal(text, 'Select Me')
+        assert.equal(text, 'def factorial(n): ')
         await textEditor.clearText()
 
+        const textBefore = await textEditor.getText()
         await workbench.executeCommand('Amazon Q: Inline Chat')
         const input = new InputBox()
-        await input.sendKeys('Write a simple sentece')
+        await input.sendKeys('Generate the fibonacci sequence through iteration')
         await input.sendKeys(Key.ENTER)
-        const driver = textEditor.getDriver()
-        await pressKey(driver, 'ENTER')
-        await pressKey(driver, 'TAB')
+        // Must wait for response to be generated.
+        await sleep(8000)
+
+        const textAfter = await textEditor.getText()
+        assert(textAfter.length > textBefore.length, 'Amazon Q should have generated code')
+        await textEditor.clearText()
     })
 })
diff --git a/packages/amazonq/test/e2e_new/amazonq/utils/generalUtils.ts b/packages/amazonq/test/e2e_new/amazonq/utils/generalUtils.ts
index b85d2e98012..d4bfc20c702 100644
--- a/packages/amazonq/test/e2e_new/amazonq/utils/generalUtils.ts
+++ b/packages/amazonq/test/e2e_new/amazonq/utils/generalUtils.ts
@@ -157,9 +157,11 @@ export async function createNewTextFile(workbench: Workbench, editorView: Editor
  * @returns Promise<void>
  */
 export async function writeToTextEditor(textEditor: TextEditor, text: string): Promise<void> {
+    // We require a "dummy" space to be written such that we can properly index the
+    // number of lines to register the textEditor.
+    await textEditor.typeTextAt(1, 1, ' ')
     const currentLines = await textEditor.getNumberOfLines()
-    const nextLine = currentLines + 1
-    await textEditor.typeTextAt(nextLine, 1, text)
+    await textEditor.typeTextAt(currentLines, 1, text)
 }
 
 /**