diff --git a/packages/app-tests/e2e/auto-placing-fields/auto-place-fields-document.spec.ts b/packages/app-tests/e2e/auto-placing-fields/auto-place-fields-document.spec.ts
new file mode 100644
index 000000000..c695261c9
--- /dev/null
+++ b/packages/app-tests/e2e/auto-placing-fields/auto-place-fields-document.spec.ts
@@ -0,0 +1,98 @@
+import { expect, test } from '@playwright/test';
+import path from 'path';
+
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../fixtures/authentication';
+
+const PLACEHOLDER_PDF_PATH = path.join(
+  __dirname,
+  '../../../assets/project-proposal-single-recipient.pdf',
+);
+test.describe('PDF Placeholders with single recipient', () => {
+  test('[AUTO_PLACING_FIELDS]: should automatically create recipients from PDF placeholders', async ({
+    page,
+  }) => {
+    const { user, team } = await seedUser();
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents`,
+    });
+
+    const fileInput = page.locator('input[type="file"]').nth(1);
+    await fileInput.waitFor({ state: 'attached' });
+    await fileInput.setInputFiles(PLACEHOLDER_PDF_PATH);
+
+    await page.waitForTimeout(3000);
+
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    await expect(page.getByRole('heading', { name: 'Add Signers' })).toBeVisible();
+    await expect(page.getByPlaceholder('Email')).toHaveValue('recipient.1@documenso.com');
+    await expect(page.getByPlaceholder('Name')).toHaveValue('Recipient 1');
+  });
+
+  test('[AUTO_PLACING_FIELDS]: should automatically place fields from PDF placeholders', async ({
+    page,
+  }) => {
+    const { user, team } = await seedUser();
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents`,
+    });
+
+    const fileInput = page.locator('input[type="file"]').nth(1);
+    await fileInput.waitFor({ state: 'attached' });
+    await fileInput.setInputFiles(PLACEHOLDER_PDF_PATH);
+
+    await page.waitForTimeout(3000);
+
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+    await expect(page.locator('[data-field-type="SIGNATURE"]')).toBeVisible();
+    await expect(page.locator('[data-field-type="EMAIL"]')).toBeVisible();
+    await expect(page.locator('[data-field-type="NAME"]')).toBeVisible();
+    await expect(page.locator('[data-field-type="TEXT"]')).toBeVisible();
+  });
+
+  test('[AUTO_PLACING_FIELDS]: should automatically configure fields from PDF placeholders', async ({
+    page,
+  }) => {
+    const { user, team } = await seedUser();
+
+    await apiSignin({
+      page,
+      email: user.email,
+      redirectPath: `/t/${team.url}/documents`,
+    });
+
+    const fileInput = page.locator('input[type="file"]').nth(1);
+    await fileInput.waitFor({ state: 'attached' });
+    await fileInput.setInputFiles(PLACEHOLDER_PDF_PATH);
+
+    await page.waitForTimeout(3000);
+
+    await page.getByRole('button', { name: 'Continue' }).click();
+    await page.getByRole('button', { name: 'Continue' }).click();
+
+    await page.getByText('Text').nth(1).click();
+    await page.getByRole('button', { name: 'Advanced settings' }).click();
+
+    await expect(page.getByRole('heading', { name: 'Advanced settings' })).toBeVisible();
+    await expect(
+      page
+        .locator('div')
+        .filter({ hasText: /^Required field$/ })
+        .getByRole('switch'),
+    ).toBeChecked();
+
+    await expect(page.getByRole('combobox')).toHaveText('Right');
+  });
+});