diff --git a/packages/typespec-vscode/test/extension/common/mock-dialogs.ts b/packages/typespec-vscode/test/extension/common/mock-dialogs.ts
index e8fd008ea2c..9c18bd73b12 100644
--- a/packages/typespec-vscode/test/extension/common/mock-dialogs.ts
+++ b/packages/typespec-vscode/test/extension/common/mock-dialogs.ts
@@ -7,6 +7,26 @@ export interface Dialog {
   }>;
 }
 
+/** Special marker to indicate a sequence of results where each call returns the next item */
+const SEQUENCE_MARKER = "__sequence__" as const;
+
+export interface DialogResultSequence<T> {
+  [SEQUENCE_MARKER]: true;
+  results: T[];
+}
+
+/** Create a sequence of results where each call returns the next item in the list */
+export function sequence<T>(...results: T[]): DialogResultSequence<T> {
+  return {
+    [SEQUENCE_MARKER]: true,
+    results,
+  };
+}
+
+function isSequence<T>(value: unknown): value is DialogResultSequence<T> {
+  return typeof value === "object" && value !== null && SEQUENCE_MARKER in value;
+}
+
 export type DialogMethodStub<T extends keyof Dialog> = {
   method: T;
   value: Awaited<ReturnType<Dialog[T]>>;
@@ -14,7 +34,14 @@ export type DialogMethodStub<T extends keyof Dialog> = {
 
 export type DialogMethodStubPartial<T extends keyof Dialog> = {
   method: T;
-  value: Partial<Awaited<ReturnType<Dialog[T]>>>;
+  value:
+    | Partial<Awaited<ReturnType<Dialog[T]>>>
+    | DialogResultSequence<Partial<Awaited<ReturnType<Dialog[T]>>>>;
+};
+
+type DialogMethodStubResolved<T extends keyof Dialog> = {
+  method: T;
+  value: Awaited<ReturnType<Dialog[T]>> | DialogResultSequence<Awaited<ReturnType<Dialog[T]>>>;
 };
 
 type DialogDefaults = {
@@ -43,30 +70,67 @@ export function stubMultipleDialogs<T extends keyof Dialog>(
 ) {
   const mocksRequired = mocks.map((mock) => {
     const methodDefault = dialogDefaults[mock.method];
-    if (!methodDefault) return mock as DialogMethodStub<T>;
+    if (!methodDefault) return mock as DialogMethodStubResolved<T>;
+
+    if (isSequence(mock.value)) {
+      // Apply defaults to each result in the sequence
+      const resolvedResults = mock.value.results.map((result) => {
+        if (typeof result === "object") {
+          return { ...methodDefault, ...result };
+        }
+        return result ?? methodDefault;
+      });
+      return {
+        method: mock.method,
+        value: { __sequence__: true, results: resolvedResults },
+      } as DialogMethodStubResolved<T>;
+    }
+
     if (typeof mock.value === "object") {
       mock.value = { ...methodDefault, ...mock.value };
     } else {
       mock.value = mock.value ?? methodDefault;
     }
-    return mock as DialogMethodStub<T>;
+    return mock as DialogMethodStubResolved<T>;
   });
 
   // https://github.com/microsoft/playwright/issues/8278#issuecomment-1009957411
-  return app.evaluate(({ dialog }, mocks) => {
+  return app.evaluate(({ dialog, ...args }, 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;
-        };
+
+      const isSeq = (v: unknown): v is { __sequence__: true; results: unknown[] } =>
+        typeof v === "object" && v !== null && "__sequence__" in v;
+
+      if (isSeq(mock.value)) {
+        let callIndex = 0;
+        const results = mock.value.results;
+        if (mock.method.endsWith("Sync")) {
+          dialog[mock.method] = () => {
+            const result = results[Math.min(callIndex, results.length - 1)];
+            callIndex++;
+
+            return result;
+          };
+        } else {
+          dialog[mock.method] = async () => {
+            const result = results[Math.min(callIndex, results.length - 1)];
+            return result;
+          };
+        }
       } else {
-        dialog[mock.method] = async () => {
-          return mock.value;
-        };
+        if (mock.method.endsWith("Sync")) {
+          dialog[mock.method] = () => {
+            return mock.value;
+          };
+        } else {
+          dialog[mock.method] = async () => {
+            return mock.value;
+          };
+        }
       }
     });
   }, mocksRequired);
@@ -74,8 +138,18 @@ export function stubMultipleDialogs<T extends keyof Dialog>(
 
 /**
  * Mock the `showOpenDialog`. Call this before something that will trigger the dialog.
+ * @param filePaths - Either a single array of file paths, or a sequence of arrays for multiple calls
  */
-export function mockShowOpenDialog(app: ElectronApplication, filePaths: string[]) {
+export function mockShowOpenDialog(
+  app: ElectronApplication,
+  filePaths: string[] | DialogResultSequence<string[]>,
+) {
+  if (isSequence(filePaths)) {
+    const sequenceValue = sequence(
+      ...filePaths.results.map((r) => ({ filePaths: r, canceled: false })),
+    );
+    return stubMultipleDialogs(app, [{ method: "showOpenDialog", value: sequenceValue }]);
+  }
   return stubDialog(app, "showOpenDialog", {
     filePaths,
     canceled: false,
diff --git a/packages/typespec-vscode/test/extension/import-typespec.test.ts b/packages/typespec-vscode/test/extension/import-typespec.test.ts
index 3e4ea9a186d..09a1f5dc3b9 100644
--- a/packages/typespec-vscode/test/extension/import-typespec.test.ts
+++ b/packages/typespec-vscode/test/extension/import-typespec.test.ts
@@ -6,9 +6,9 @@ import {
   packagesInstall,
   packPackages,
   preContrastResult,
-  startWithRightClick,
+  startWithCommandPalette,
 } from "./common/common-steps";
-import { mockShowOpenDialog } from "./common/mock-dialogs";
+import { mockShowOpenDialog, sequence } from "./common/mock-dialogs";
 import { CaseScreenshot, tempDir, test, testfilesDir } from "./common/utils";
 
 // Test files are copied into the temporary directory before tests run
@@ -85,9 +85,10 @@ describe.each(ImportCasesConfigList)("ImportTypespecFromOpenApi3", async (item)
     const { page, app } = await launch({
       workspacePath,
     });
+    const targetPath = path.resolve(workspacePath, "ImportTypespecProjectEmptyFolder");
     const openapifilepath = path.resolve(ImportTypespecProjectFolderPath, "openapi.3.0.yaml");
-    await mockShowOpenDialog(app, [openapifilepath]);
-    await startWithRightClick(page, "Import TypeSpec from Openapi 3", cs);
+    await mockShowOpenDialog(app, sequence([targetPath], [openapifilepath]));
+    await startWithCommandPalette(page, "Import TypeSpec from Openapi 3", cs);
 
     await preContrastResult(
       page,
@@ -97,8 +98,8 @@ describe.each(ImportCasesConfigList)("ImportTypespecFromOpenApi3", async (item)
       cs,
       app,
     );
-    const resultFilePath = path.resolve(workspacePath, "./ImportTypespecProjectEmptyFolder");
-    await expectFilesInDir(expectedResults, resultFilePath);
+
+    await expectFilesInDir(expectedResults, targetPath);
     app.close();
   });
 });