diff --git a/apps/web/playwright/onboarding.e2e.ts b/apps/web/playwright/onboarding.e2e.ts
index 72696117aa..b516f9e693 100644
--- a/apps/web/playwright/onboarding.e2e.ts
+++ b/apps/web/playwright/onboarding.e2e.ts
@@ -1,157 +1,80 @@
+/* eslint-disable playwright/no-skipped-test */
 import { expect } from "@playwright/test";
 import { UserPlan } from "@prisma/client";
 
 import { test } from "./lib/fixtures";
 
-test.describe.configure({ mode: "parallel" });
+test.describe.configure({ mode: "serial" });
 
 test.describe("Onboarding", () => {
   test.describe("Onboarding v2", () => {
-    test("test onboarding v2 new user first step", async ({ page, users }) => {
-      const user = await users.create({ plan: UserPlan.TRIAL, completedOnboarding: false, name: "new user" });
+    test("Onboarding Flow", async ({ page, users }) => {
+      const user = await users.create({ plan: UserPlan.TRIAL, completedOnboarding: false, name: null });
       await user.login();
-      await page.goto("/getting-started");
 
-      // First step
-      const usernameInput = await page.locator("input[name=username]");
-      await usernameInput.fill("new user onboarding");
+      // tests whether the user makes it to /getting-started
+      // after login with completedOnboarding false
+      await page.waitForURL("/getting-started");
 
-      const nameInput = await page.locator("input[name=name]");
-      await nameInput.fill("new user 2");
+      await test.step("step 1", async () => {
+        // Check required fields
+        await page.locator("button[type=submit]").click();
+        await expect(page.locator("data-testid=required")).toBeVisible();
 
-      const timezoneSelect = await page.locator("input[role=combobox]");
-      await timezoneSelect.click();
-      const timezoneOption = await page.locator("text=Eastern Time");
-      await timezoneOption.click();
+        // happy path
+        await page.locator("input[name=username]").fill("new user onboarding");
+        await page.locator("input[name=name]").fill("new user 2");
+        await page.locator("input[role=combobox]").click();
+        await page.locator("text=Eastern Time").click();
 
-      const nextButtonUserProfile = await page.locator("button[type=submit]");
-      await nextButtonUserProfile.click();
+        await page.locator("button[type=submit]").click();
 
-      await expect(page).toHaveURL(/.*connected-calendar/);
+        // should be on step 2 now.
+        await expect(page).toHaveURL(/.*connected-calendar/);
 
-      const userComplete = await user.self();
-      expect(userComplete.name).toBe("new user 2");
-    });
-
-    test("test onboarding v2 new user second step", async ({ page, users }) => {
-      const user = await users.create({ plan: UserPlan.TRIAL, completedOnboarding: false, name: "new user" });
-      await user.login();
-      await page.goto("/getting-started/connected-calendar");
-
-      // Second step
-      const nextButtonCalendar = await page.locator("button[data-testid=save-calendar-button]");
-      const isDisabled = await nextButtonCalendar.isDisabled();
-      await expect(isDisabled).toBe(true);
-
-      const skipStepButton = await page.locator("button[data-testid=skip-step]");
-      await skipStepButton.click();
-      await expect(page).toHaveURL(/.*setup-availability/);
-      // @TODO: make sure calendar UL list has at least 1 item
-    });
-
-    test("test onboarding v2 new user third step", async ({ page, users }) => {
-      const user = await users.create({ plan: UserPlan.TRIAL, completedOnboarding: false, name: "new user" });
-      await user.login();
-      await page.goto("/getting-started/setup-availability");
-
-      // Third step
-
-      const nextButtonAvailability = await page.locator("button[data-testid=save-availability]");
-      const isDisabled = await nextButtonAvailability.isDisabled();
-      await expect(isDisabled).toBe(false);
-
-      const skipStepButton = await page.locator("button[data-testid=skip-step]");
-      await skipStepButton.click();
-      await expect(page).toHaveURL(/.*user-profile/);
-    });
-
-    test("test onboarding v2 new user fourth step", async ({ page, users }) => {
-      const user = await users.create({ plan: UserPlan.TRIAL, completedOnboarding: false, name: "new user" });
-      await user.login();
-      await page.goto("/getting-started/user-profile");
-
-      // Fourth step
-
-      const finishButton = await page.locator("button[type=submit]");
-      const bioInput = await page.locator("textarea[name=bio]");
-      await bioInput.fill("Something about me");
-      const isDisabled = await finishButton.isDisabled();
-      await expect(isDisabled).toBe(false);
-      await finishButton.click();
-
-      await expect(page).toHaveURL(/.*event-types/);
-
-      const userComplete = await user.self();
-      expect(userComplete.bio).toBe("Something about me");
-    });
-  });
-
-  test.describe("Onboarding v2 required field test", () => {
-    test("test onboarding v2 new user first step required fields", async ({ page, users }) => {
-      const user = await users.create({
-        plan: UserPlan.TRIAL,
-        completedOnboarding: false,
-        name: null,
-        username: null,
+        const userComplete = await user.self();
+        expect(userComplete.name).toBe("new user 2");
       });
 
-      await user.login();
-      await page.goto("/getting-started");
+      await test.step("step 2", async () => {
+        const isDisabled = await page.locator("button[data-testid=save-calendar-button]").isDisabled();
+        await expect(isDisabled).toBe(true);
+        // tests skip button, we don't want to test entire flow.
+        await page.locator("button[data-testid=skip-step]").click();
 
-      // First step
-      const nextButtonUserProfile = await page.locator("button[type=submit]");
-      await nextButtonUserProfile.click();
-
-      const requiredName = await page.locator("data-testid=required");
-      await expect(requiredName).toBeVisible();
-    });
-
-    test("test onboarding v2 new user fourth step required fields", async ({ page, users }) => {
-      const user = await users.create({
-        plan: UserPlan.TRIAL,
-        completedOnboarding: false,
+        await expect(page).toHaveURL(/.*setup-availability/);
       });
 
-      await user.login();
-      await page.goto("/getting-started/user-profile");
+      await test.step("step 3", async () => {
+        const isDisabled = await page.locator("button[data-testid=save-availability]").isDisabled();
+        await expect(isDisabled).toBe(false);
+        // same here, skip this step.
+        await page.locator("button[data-testid=skip-step]").click();
 
-      // Fourth step
+        await expect(page).toHaveURL(/.*user-profile/);
+      });
 
-      const finishButton = await page.locator("button[type=submit]");
-      await finishButton.click();
+      await test.step("step 4", async () => {
+        const finishButton = await page.locator("button[type=submit]");
+        // bio field is required, try to submit (and test whether that fails)
+        await finishButton.click();
 
-      const requiredBio = await page.locator("data-testid=required");
-      await expect(requiredBio).toBeVisible();
+        const requiredBio = await page.locator("data-testid=required");
+        await expect(requiredBio).toBeVisible();
+
+        await page.locator("textarea[name=bio]").fill("Something about me");
+
+        const isDisabled = await finishButton.isDisabled();
+        await expect(isDisabled).toBe(false);
+
+        await finishButton.click();
+
+        // should redirect to /event-types after onboarding
+        await page.waitForURL("/event-types");
+
+        const userComplete = await user.self();
+        expect(userComplete.bio).toBe("Something about me");
+      });
     });
   });
-
-  test.describe("Onboarding redirects", () => {
-    test("redirects to /getting-started after login", async ({ page }) => {
-      await page.goto("/event-types");
-      await page.waitForNavigation();
-    });
-
-    // @TODO: temporary disabled due to flakiness
-    // test("test onboarding v2 new user simulate add calendar redirect", async ({ page, users }) => {
-    //   const user = await users.create({
-    //     plan: UserPlan.TRIAL,
-    //     completedOnboarding: false,
-    //   });
-
-    //   await user.login();
-    //   const url = await page.url();
-    //   await page.context().addCookies([
-    //     {
-    //       name: "return-to",
-    //       value: "/getting-started/connected-calendar",
-    //       expires: 9999999999,
-    //       url,
-    //     },
-    //   ]);
-
-    //   await page.goto("/apps/installed");
-
-    //   await expect(page).toHaveURL(/.*connected-calendar/);
-    // });
-  });
 });