diff --git a/packages/typespec-vscode/test/extension/common/common-steps.ts b/packages/typespec-vscode/test/extension/common/common-steps.ts
index fd4fffb580f..d05e2db33ee 100644
--- a/packages/typespec-vscode/test/extension/common/common-steps.ts
+++ b/packages/typespec-vscode/test/extension/common/common-steps.ts
@@ -26,7 +26,6 @@ export async function preContrastResult(
     await page.waitForSelector(`:text("${text}")`, { timeout });
   } catch (e) {
     await cs.screenshot(page, "error");
-    app.close();
     throw new Error(`${errorMessage} - Timed out waiting for text: "${text}" - ${e}`, { cause: e });
   }
 }
diff --git a/packages/typespec-vscode/test/extension/common/mock-dialogs.ts b/packages/typespec-vscode/test/extension/common/mock-dialogs.ts
index e8fd008ea2c..d9950b34573 100644
--- a/packages/typespec-vscode/test/extension/common/mock-dialogs.ts
+++ b/packages/typespec-vscode/test/extension/common/mock-dialogs.ts
@@ -37,7 +37,7 @@ export function stubDialog<T extends keyof Dialog>(
   return stubMultipleDialogs(app, [{ method, value }]);
 }
 
-export function stubMultipleDialogs<T extends keyof Dialog>(
+export async function stubMultipleDialogs<T extends keyof Dialog>(
   app: ElectronApplication,
   mocks: DialogMethodStubPartial<T>[],
 ) {
@@ -53,23 +53,40 @@ export function stubMultipleDialogs<T extends keyof Dialog>(
   });
 
   // https://github.com/microsoft/playwright/issues/8278#issuecomment-1009957411
-  return app.evaluate(({ dialog }, mocks) => {
-    mocks.forEach((mock) => {
-      const thisDialog = dialog[mock.method];
-      if (!thisDialog) {
-        throw new Error(`can't find ${mock.method} on dialog module.`);
-      }
-      if (mock.method.endsWith("Sync")) {
-        dialog[mock.method] = () => {
-          return mock.value;
-        };
-      } else {
-        dialog[mock.method] = async () => {
-          return mock.value;
-        };
+  // Retry to handle transient "Execution context was destroyed" errors
+  // that occur when VS Code reloads during startup.
+  const maxRetries = 3;
+  const retryDelayMs = 1000;
+
+  for (let attempt = 1; attempt <= maxRetries; attempt++) {
+    try {
+      return await app.evaluate(({ dialog }, mocks) => {
+        mocks.forEach((mock) => {
+          const thisDialog = dialog[mock.method];
+          if (!thisDialog) {
+            throw new Error(`can't find ${mock.method} on dialog module.`);
+          }
+          if (mock.method.endsWith("Sync")) {
+            dialog[mock.method] = () => {
+              return mock.value;
+            };
+          } else {
+            dialog[mock.method] = async () => {
+              return mock.value;
+            };
+          }
+        });
+      }, mocksRequired);
+    } catch (error: any) {
+      const isRetryable =
+        error.message?.includes("Execution context was destroyed") ||
+        error.message?.includes("Target page, context or browser has been closed");
+      if (!isRetryable || attempt === maxRetries) {
+        throw error;
       }
-    });
-  }, mocksRequired);
+      await new Promise((resolve) => setTimeout(resolve, retryDelayMs));
+    }
+  }
 }
 
 /**
diff --git a/packages/typespec-vscode/test/extension/common/utils.ts b/packages/typespec-vscode/test/extension/common/utils.ts
index 1624d8332bd..edd66d6ef9e 100644
--- a/packages/typespec-vscode/test/extension/common/utils.ts
+++ b/packages/typespec-vscode/test/extension/common/utils.ts
@@ -59,7 +59,18 @@ export const test = baseTest.extend<{
           `--folder-uri=file:${path.resolve(workspacePath)}`,
         ].filter((v): v is string => !!v),
       });
+
+      // Ensure Electron is always closed on teardown, even if later steps fail.
+      teardowns.push(async () => {
+        try {
+          await app.close();
+        } catch (error) {}
+      });
+
       const page = await app.firstWindow();
+      // Wait for the page to fully load to reduce the chance of
+      // VS Code reloading the window and destroying the execution context.
+      await page.waitForLoadState("domcontentloaded");
       const tracePath = join(projectRoot, "test-results", task.name, "trace.zip");
       const artifactsDir = join(tempDir, "playwright-artifacts");
       await fs.promises.mkdir(artifactsDir, { recursive: true }); // make sure the directory exists
diff --git a/packages/typespec-vscode/test/extension/create-typespec.test.ts b/packages/typespec-vscode/test/extension/create-typespec.test.ts
index cdbc7afefe5..c08dbefe414 100644
--- a/packages/typespec-vscode/test/extension/create-typespec.test.ts
+++ b/packages/typespec-vscode/test/extension/create-typespec.test.ts
@@ -69,6 +69,9 @@ describe.each(CreateCasesConfigList)("CreateTypespecProject", async (item) => {
       workspacePath: workspacePath,
     });
     await cs.screenshot(page, "after_launch");
+    // Wait for VS Code UI to be ready before mocking dialogs to avoid
+    // "Execution context was destroyed" errors from window reloads.
+    await page.waitForSelector(".explorer-viewlet", { timeout: 30000 });
     await mockShowOpenDialog(app, [workspacePath]);
     await startWithCommandPalette(page, "Create Typespec Project", cs);
     await cs.screenshot(page, "after_start_command");
@@ -86,6 +89,5 @@ describe.each(CreateCasesConfigList)("CreateTypespecProject", async (item) => {
       app,
     );
     await expectFilesInDir(expectedResults, workspacePath);
-    app.close();
   });
 });
diff --git a/packages/typespec-vscode/test/extension/emit-typespec.test.ts b/packages/typespec-vscode/test/extension/emit-typespec.test.ts
index 5f4e9ad2ae4..6cffcf0d599 100644
--- a/packages/typespec-vscode/test/extension/emit-typespec.test.ts
+++ b/packages/typespec-vscode/test/extension/emit-typespec.test.ts
@@ -104,6 +104,5 @@ describe.each(EmitCasesConfigList)("EmitTypespecProject", async (item) => {
     }
     const resultFilePath = path.resolve(workspacePath, "./tsp-output/@typespec");
     await expectFilesInDir(expectedResults, resultFilePath);
-    app.close();
   });
 });
diff --git a/packages/typespec-vscode/test/extension/import-typespec.test.ts b/packages/typespec-vscode/test/extension/import-typespec.test.ts
index 3e4ea9a186d..1bc2cb2e653 100644
--- a/packages/typespec-vscode/test/extension/import-typespec.test.ts
+++ b/packages/typespec-vscode/test/extension/import-typespec.test.ts
@@ -99,6 +99,5 @@ describe.each(ImportCasesConfigList)("ImportTypespecFromOpenApi3", async (item)
     );
     const resultFilePath = path.resolve(workspacePath, "./ImportTypespecProjectEmptyFolder");
     await expectFilesInDir(expectedResults, resultFilePath);
-    app.close();
   });
 });
diff --git a/packages/typespec-vscode/test/extension/preview-typespec.test.ts b/packages/typespec-vscode/test/extension/preview-typespec.test.ts
index 1e11cf61ace..587af2315d8 100644
--- a/packages/typespec-vscode/test/extension/preview-typespec.test.ts
+++ b/packages/typespec-vscode/test/extension/preview-typespec.test.ts
@@ -58,7 +58,7 @@ describe.each(PreviewCasesConfigList)("PreviewAPIDocument", async (item) => {
   test(caseName, async ({ launch }) => {
     const cs = new CaseScreenshot(caseName);
     const workspacePath = PreviewTypespecProjectFolderPath;
-    const { page, app } = await launch({
+    const { page } = await launch({
       workspacePath,
     });
     await page.getByRole("treeitem", { name: "main.tsp" }).locator("a").click();
@@ -80,6 +80,5 @@ describe.each(PreviewCasesConfigList)("PreviewAPIDocument", async (item) => {
       cs,
     );
     await rm(cs.caseDir, { recursive: true });
-    app.close();
   });
 });