diff --git a/apps/web/tests/authentication.spec.ts b/apps/web/tests/authentication.spec.ts
index 8176af0c9..24cf11c40 100644
--- a/apps/web/tests/authentication.spec.ts
+++ b/apps/web/tests/authentication.spec.ts
@@ -3,21 +3,11 @@ import { prisma } from "@rallly/database";
 import { load } from "cheerio";
 
 import { captureEmailHTML } from "./mailpit/mailpit";
+import { RegisterPage } from "./register-page";
+import { getCode } from "./utils";
 
 const testUserEmail = "test@example.com";
 
-/**
- * Get the 6-digit code from the email
- * @returns 6-digit code
- */
-const getCode = async () => {
-  const html = await captureEmailHTML(testUserEmail);
-
-  const $ = load(html);
-
-  return $("#code").text().trim();
-};
-
 test.describe.serial(() => {
   test.afterAll(async () => {
     try {
@@ -49,26 +39,11 @@ test.describe.serial(() => {
     });
 
     test("user registration", async ({ page }) => {
-      await page.goto("/register");
-
-      await page.getByText("Create Your Account").waitFor();
-
-      await page.getByPlaceholder("Jessie Smith").fill("Test User");
-      await page
-        .getByPlaceholder("jessie.smith@example.com")
-        .fill(testUserEmail);
-
-      await page.getByRole("button", { name: "Continue", exact: true }).click();
-
-      const code = await getCode();
-
-      await page.getByText("Finish Registering").waitFor();
-
-      const codeInput = page.getByPlaceholder("Enter your 6-digit code");
-
-      await codeInput.fill(code);
-
-      await expect(page.getByText("Test User")).toBeVisible();
+      const registerPage = new RegisterPage(page);
+      await registerPage.register({
+        name: "Test User",
+        email: testUserEmail,
+      });
     });
   });
 
@@ -141,7 +116,7 @@ test.describe.serial(() => {
 
       await page.getByRole("button", { name: "Continue with Email" }).click();
 
-      const code = await getCode();
+      const code = await getCode(testUserEmail);
 
       await page.getByPlaceholder("Enter your 6-digit code").fill(code);
 
@@ -157,7 +132,7 @@ test.describe.serial(() => {
 
       await page.getByRole("button", { name: "Continue with Email" }).click();
 
-      const code = await getCode();
+      const code = await getCode(testUserEmail);
 
       await page.getByPlaceholder("Enter your 6-digit code").fill(code);
 
diff --git a/apps/web/tests/create-delete-poll.spec.ts b/apps/web/tests/create-delete-poll.spec.ts
index e3ed1b6e5..3c5fdfcc8 100644
--- a/apps/web/tests/create-delete-poll.spec.ts
+++ b/apps/web/tests/create-delete-poll.spec.ts
@@ -15,7 +15,6 @@ test.describe.serial(() => {
   test("create a new poll", async () => {
     const newPollPage = new NewPollPage(page);
 
-    await newPollPage.goto();
     await newPollPage.createPollAndCloseDialog();
 
     await expect(page.getByTestId("poll-title")).toHaveText("Monthly Meetup");
diff --git a/apps/web/tests/guest-to-user-migration.spec.ts b/apps/web/tests/guest-to-user-migration.spec.ts
new file mode 100644
index 000000000..7178ed210
--- /dev/null
+++ b/apps/web/tests/guest-to-user-migration.spec.ts
@@ -0,0 +1,49 @@
+import { expect, test } from "@playwright/test";
+import { prisma } from "@rallly/database";
+import { NewPollPage } from "tests/new-poll-page";
+
+import { deleteAllMessages } from "./mailpit/mailpit";
+import { RegisterPage } from "./register-page";
+
+const TEST_USER_EMAIL = "testuser@example.com";
+
+test.describe.serial(() => {
+  test.beforeAll(async () => {
+    await deleteAllMessages();
+  });
+
+  test.afterAll(async () => {
+    // Clean up the test user
+    await prisma.user.delete({
+      where: {
+        email: TEST_USER_EMAIL,
+      },
+    });
+  });
+
+  test("guest user can create a poll and convert to registered user", async ({
+    page,
+  }) => {
+    // Step 1: Create a poll as guest
+    const newPollPage = new NewPollPage(page);
+    await newPollPage.createPollAndCloseDialog();
+    await expect(page.getByTestId("poll-title")).toHaveText("Monthly Meetup");
+
+    // Step 2: Navigate to registration
+    await page.click("text=Create an account");
+    await expect(page).toHaveURL(/register/);
+
+    // Step 3: Complete registration
+    const registerPage = new RegisterPage(page);
+    await registerPage.register({
+      name: "Test User",
+      email: TEST_USER_EMAIL,
+    });
+
+    // Step 4: Navigate back to the poll
+    await page.getByRole("link", { name: "Live" }).click();
+    await expect(page).toHaveURL(/polls/);
+    await page.click("text=Monthly Meetup");
+    await expect(page.getByTestId("poll-title")).toHaveText("Monthly Meetup");
+  });
+});
diff --git a/apps/web/tests/new-poll-page.ts b/apps/web/tests/new-poll-page.ts
index 9d1151d13..31b002964 100644
--- a/apps/web/tests/new-poll-page.ts
+++ b/apps/web/tests/new-poll-page.ts
@@ -9,6 +9,7 @@ export class NewPollPage {
   }
 
   async createPollAndCloseDialog() {
+    await this.goto();
     const pollPage = await this.createPoll();
     await pollPage.closeDialog();
     return pollPage;
diff --git a/apps/web/tests/register-page.ts b/apps/web/tests/register-page.ts
new file mode 100644
index 000000000..19aa74bcb
--- /dev/null
+++ b/apps/web/tests/register-page.ts
@@ -0,0 +1,32 @@
+import type { Page } from "@playwright/test";
+import { expect } from "@playwright/test";
+
+import { getCode } from "./utils";
+
+export class RegisterPage {
+  constructor(private readonly page: Page) {}
+
+  async goto() {
+    await this.page.goto("/register");
+    await this.page.getByText("Create Your Account").waitFor();
+  }
+
+  async register({ name, email }: { name: string; email: string }) {
+    await this.goto();
+    // Fill in registration form
+    await this.page.getByPlaceholder("Jessie Smith").fill(name);
+    await this.page.getByPlaceholder("jessie.smith@example.com").fill(email);
+
+    await this.page
+      .getByRole("button", { name: "Continue", exact: true })
+      .click();
+
+    // Handle verification code
+    const code = await getCode(email);
+    await this.page.getByText("Finish Registering").waitFor();
+    await this.page.getByPlaceholder("Enter your 6-digit code").fill(code);
+
+    // Verify successful registration
+    await expect(this.page.getByText(name)).toBeVisible();
+  }
+}
diff --git a/apps/web/tests/utils.ts b/apps/web/tests/utils.ts
new file mode 100644
index 000000000..3a94ab8da
--- /dev/null
+++ b/apps/web/tests/utils.ts
@@ -0,0 +1,16 @@
+import { load } from "cheerio";
+
+import { captureEmailHTML } from "./mailpit/mailpit";
+
+/**
+ * Get the 6-digit code from the email
+ * @param email The email address to get the code for
+ * @returns 6-digit code
+ */
+export const getCode = async (email: string) => {
+  const html = await captureEmailHTML(email);
+
+  const $ = load(html);
+
+  return $("#code").text().trim();
+};