diff --git a/e2e/completion-modal.spec.ts b/e2e/completion-modal.spec.ts
index 65b9494c2bb..063639d87d0 100644
--- a/e2e/completion-modal.spec.ts
+++ b/e2e/completion-modal.spec.ts
@@ -1,6 +1,7 @@
 import { test, expect } from '@playwright/test';
 import translations from '../client/i18n/locales/english/translations.json';
 import { authedRequest } from './utils/request';
+import { allowTrailingSlash } from './utils/url';
 
 const nextChallengeURL =
   '/learn/data-analysis-with-python/data-analysis-with-python-projects/demographic-data-analyzer';
@@ -72,7 +73,7 @@ test.describe('Challenge Completion Modal Tests (Signed Out)', () => {
     await page
       .getByRole('link', { name: translations.learn['sign-in-save'] })
       .click();
-    await expect(page).toHaveURL(/.*\/learn\/?$/);
+    await expect(page).toHaveURL(allowTrailingSlash('/learn'));
   });
 
   test('should redirect to next challenge', async ({ page }) => {
diff --git a/e2e/delete-modal.spec.ts b/e2e/delete-modal.spec.ts
index b58b098418b..7d060dc44be 100644
--- a/e2e/delete-modal.spec.ts
+++ b/e2e/delete-modal.spec.ts
@@ -5,6 +5,7 @@ import { test, expect } from '@playwright/test';
 
 import translations from '../client/i18n/locales/english/translations.json';
 import { alertToBeVisible } from './utils/alerts';
+import { allowTrailingSlash } from './utils/url';
 
 const execP = promisify(exec);
 
@@ -145,7 +146,7 @@ test.describe('Delete Modal component', () => {
       })
     ).not.toBeVisible();
 
-    await expect(page).toHaveURL(/.*\/learn\/?/);
+    await expect(page).toHaveURL(allowTrailingSlash('/learn'));
     await alertToBeVisible(page, translations.flash['account-deleted']);
     // The user is signed out after their account is deleted
     await expect(page.getByRole('link', { name: 'Sign in' })).toHaveCount(2);
diff --git a/e2e/donation-modal.spec.ts b/e2e/donation-modal.spec.ts
index 3ad2f31d556..a5c42d87516 100644
--- a/e2e/donation-modal.spec.ts
+++ b/e2e/donation-modal.spec.ts
@@ -3,6 +3,7 @@ import { test, expect, type Page } from '@playwright/test';
 import { addGrowthbookCookie } from './utils/add-growthbook-cookie';
 
 import { clearEditor, focusEditor } from './utils/editor';
+import { allowTrailingSlash } from './utils/url';
 
 const slowExpect = expect.configure({ timeout: 25000 });
 
@@ -22,7 +23,9 @@ const completeFrontEndCert = async (page: Page, number?: number) => {
   const loopNumber = number || projects.length;
   for (let i = 0; i < loopNumber; i++) {
     await page.waitForURL(
-      `/learn/front-end-development-libraries/front-end-development-libraries-projects/build-a-${projects[i]}`
+      allowTrailingSlash(
+        `/learn/front-end-development-libraries/front-end-development-libraries-projects/build-a-${projects[i]}`
+      )
     );
     await page
       .getByRole('textbox', { name: 'solution' })
@@ -92,7 +95,7 @@ const completeChallenges = async ({
 }) => {
   await page.goto(challenges[0].url);
   for (const challenge of challenges.slice(0, number)) {
-    await page.waitForURL(challenge.url);
+    await page.waitForURL(allowTrailingSlash(challenge.url));
     await focusEditor({ page, isMobile });
     await clearEditor({ page, browserName });
     await page.evaluate(
diff --git a/e2e/quincy-email-sign-up.spec.ts b/e2e/quincy-email-sign-up.spec.ts
index f21431bbc50..1ee51c19aed 100644
--- a/e2e/quincy-email-sign-up.spec.ts
+++ b/e2e/quincy-email-sign-up.spec.ts
@@ -3,6 +3,7 @@ import { execSync } from 'child_process';
 import { test, expect } from '@playwright/test';
 
 import translations from '../client/i18n/locales/english/translations.json';
+import { allowTrailingSlash } from './utils/url';
 
 const apiLocation = process.env.API_LOCATION || 'http://localhost:3000';
 
@@ -73,7 +74,7 @@ test.describe('Email sign-up page when user is not signed in', () => {
 
     // The user is signed in and automatically redirected to /learn after clicking the button.
     // We wait for this navigation to complete before moving onto the next.
-    await page.waitForURL('**/learn');
+    await page.waitForURL(allowTrailingSlash('/learn'));
     await expect(
       page.getByRole('heading', { name: 'Welcome back, Full Stack User' })
     ).toBeVisible();
@@ -144,7 +145,7 @@ test.describe('Email sign-up page when user is signed in', () => {
 
     // The user is signed in and automatically redirected to /learn after clicking the button.
     // We wait for the navigation to complete.
-    await page.waitForURL('**/learn');
+    await page.waitForURL('/learn');
     await expect(
       page.getByRole('heading', { name: 'Welcome back, Full Stack User' })
     ).toBeVisible();
@@ -180,7 +181,7 @@ test.describe('Email sign-up page when user is signed in', () => {
 
     // The user is signed in and automatically redirected to /learn after clicking the button.
     // We wait for the navigation to complete.
-    await page.waitForURL('**/learn');
+    await page.waitForURL('/learn');
     await expect(
       page.getByRole('heading', { name: 'Welcome back, Full Stack User' })
     ).toBeVisible();
diff --git a/e2e/quiz-challenge.spec.ts b/e2e/quiz-challenge.spec.ts
index 5263910feca..b0d333990ff 100644
--- a/e2e/quiz-challenge.spec.ts
+++ b/e2e/quiz-challenge.spec.ts
@@ -1,4 +1,5 @@
 import { test, expect } from '@playwright/test';
+import { allowTrailingSlash } from './utils/url';
 
 test.describe('Quiz challenge', () => {
   test.beforeEach(async ({ page }) => {
@@ -66,7 +67,9 @@ test.describe('Quiz challenge', () => {
 
     // The navigation should be blocked, the user should stay on the same page
     await expect(page).toHaveURL(
-      '/learn/full-stack-developer/quiz-basic-html/quiz-basic-html'
+      allowTrailingSlash(
+        '/learn/full-stack-developer/quiz-basic-html/quiz-basic-html'
+      )
     );
 
     await expect(page.getByRole('dialog')).toBeVisible();
diff --git a/e2e/redirect.spec.ts b/e2e/redirect.spec.ts
index 3c15b80cea9..4b349504a71 100644
--- a/e2e/redirect.spec.ts
+++ b/e2e/redirect.spec.ts
@@ -1,4 +1,5 @@
 import { test, expect } from '@playwright/test';
+import { allowTrailingSlash } from './utils/url';
 
 // To run this test locally you will need to run: pnpm run start-ci;
 // Also, make sure that you have pm2 installed globally via: pnpm install -g pm2
@@ -74,7 +75,7 @@ test.describe('Legacy Challenge Path Redirection Tests', () => {
   for (const [input, expected] of pathsToTest) {
     test(`should redirect from ${input} to ${expected}`, async ({ page }) => {
       await page.goto(input);
-      await expect(page).toHaveURL(new RegExp(`${expected}/?`));
+      await expect(page).toHaveURL(allowTrailingSlash(expected));
     });
   }
 });
diff --git a/e2e/signout-modal.spec.ts b/e2e/signout-modal.spec.ts
index 9f9e30126fe..4c90cc8542c 100644
--- a/e2e/signout-modal.spec.ts
+++ b/e2e/signout-modal.spec.ts
@@ -1,5 +1,6 @@
 import { test, expect } from '@playwright/test';
 import translations from '../client/i18n/locales/english/translations.json';
+import { allowTrailingSlash } from './utils/url';
 
 test.beforeEach(async ({ page }) => {
   await page.goto('/');
@@ -49,7 +50,7 @@ test.describe('Signout Modal component', () => {
     await expect(
       page.getByRole('dialog', { name: translations.signout.heading })
     ).not.toBeVisible();
-    await expect(page).toHaveURL(/.*\/learn\/?$/);
+    await expect(page).toHaveURL(allowTrailingSlash('/learn'));
   });
 
   test('closes modal after user cancels signing out', async ({ page }) => {
diff --git a/e2e/update-email.spec.ts b/e2e/update-email.spec.ts
index 43435001f7d..5c87322bbb7 100644
--- a/e2e/update-email.spec.ts
+++ b/e2e/update-email.spec.ts
@@ -1,5 +1,6 @@
 import { test, expect } from '@playwright/test';
 import translations from '../client/i18n/locales/english/translations.json';
+import { allowTrailingSlash } from './utils/url';
 
 test.describe('The update-email page when the user is signed in', () => {
   test.beforeEach(async ({ page }) => {
@@ -64,7 +65,7 @@ test.describe('The update-email page when the user is not signed in', () => {
     // Ref: https://github.com/microsoft/playwright/issues/20749
     test.skip(browserName === 'firefox');
 
-    await page.waitForURL(/\/learn\/?/);
+    await page.waitForURL(allowTrailingSlash('/learn'));
 
     await expect(
       page.getByRole('heading', { name: 'Welcome back, Full Stack User' })
diff --git a/e2e/utils/url.ts b/e2e/utils/url.ts
new file mode 100644
index 00000000000..053061055e1
--- /dev/null
+++ b/e2e/utils/url.ts
@@ -0,0 +1 @@
+export const allowTrailingSlash = (url: string) => RegExp(url + '[/]?$');