diff --git a/packages/app-tests/e2e/templates-flow/template-signers-step.spec.ts b/packages/app-tests/e2e/templates-flow/template-signers-step.spec.ts
index 3ce52c55c..4da9a9d12 100644
--- a/packages/app-tests/e2e/templates-flow/template-signers-step.spec.ts
+++ b/packages/app-tests/e2e/templates-flow/template-signers-step.spec.ts
@@ -98,3 +98,135 @@ test('[TEMPLATE_FLOW]: add placeholder', async ({ page }) => {
   // Advanced settings should not be visible for non EE users.
   await expect(page.getByLabel('Show advanced settings')).toBeHidden();
 });
+
+test('[TEMPLATE_FLOW]: duplicate recipients', async ({ page }) => {
+  const user = await seedUser();
+  const template = await seedBlankTemplate(user);
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/templates/${template.id}/edit`,
+  });
+
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholder' })).toBeVisible();
+
+  await page.getByPlaceholder('Email').fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').fill('Recipient');
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  await page.getByPlaceholder('Email').nth(1).fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').nth(1).fill('Recipient');
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  await page.getByPlaceholder('Email').nth(2).fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').nth(2).fill('Recipient');
+
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+  await page.getByRole('button', { name: 'Go Back' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholder' })).toBeVisible();
+});
+
+test('[TEMPLATE_FLOW]: same email different roles', async ({ page }) => {
+  const user = await seedUser();
+  const template = await seedBlankTemplate(user);
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/templates/${template.id}/edit`,
+  });
+
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholder' })).toBeVisible();
+
+  // Add a signer
+  await page.getByPlaceholder('Email').fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').fill('Documenso Recipient');
+  await page.getByRole('combobox').click();
+  await page.getByLabel('Needs to sign').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Add an approver
+  await page.getByPlaceholder('Email').nth(1).fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').nth(1).fill('Documenso Recipient');
+  await page.getByRole('combobox').nth(1).click();
+  await page.getByLabel('Needs to approve').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Add a viewer
+  await page.getByPlaceholder('Email').nth(2).fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').nth(2).fill('Documenso Recipient');
+  await page.getByRole('combobox').nth(2).click();
+  await page.getByLabel('Needs to view').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Add a CC
+  await page.getByPlaceholder('Email').nth(3).fill('recipient@documenso.com');
+  await page.getByPlaceholder('Name').nth(3).fill('Documenso Recipient');
+  await page.getByRole('combobox').nth(3).click();
+  await page.getByLabel('Receives copy').click();
+
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+  await page.getByRole('button', { name: 'Go Back' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholder' })).toBeVisible();
+});
+
+test('[TEMPLATE_FLOW]: mixed recipients', async ({ page }) => {
+  const user = await seedUser();
+  const template = await seedBlankTemplate(user);
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/templates/${template.id}/edit`,
+  });
+
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholder' })).toBeVisible();
+
+  // First recipient (unique)
+  await page.getByPlaceholder('Email').fill('recipient1@documenso.com');
+  await page.getByPlaceholder('Name').fill('First Recipient');
+  await page.getByRole('combobox').click();
+  await page.getByLabel('Needs to approve').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Second recipient (duplicate of first)
+  await page.getByPlaceholder('Email').nth(1).fill('recipient1@documenso.com');
+  await page.getByPlaceholder('Name').nth(1).fill('First Recipient');
+  await page.getByRole('combobox').nth(1).click();
+  await page.getByLabel('Needs to view').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Third recipient (unique)
+  await page.getByPlaceholder('Email').nth(2).fill('recipient2@documenso.com');
+  await page.getByPlaceholder('Name').nth(2).fill('Second Recipient');
+  await page.getByRole('combobox').nth(2).click();
+  await page.getByLabel('Needs to sign').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Fourth recipient (duplicate of first)
+  await page.getByPlaceholder('Email').nth(3).fill('recipient1@documenso.com');
+  await page.getByPlaceholder('Name').nth(3).fill('First Recipient');
+  await page.getByRole('combobox').nth(3).click();
+  await page.getByLabel('Receives copy').click();
+  await page.getByRole('button', { name: 'Add Placeholder Recipient' }).click();
+
+  // Fifth recipient (unique)
+  await page.getByPlaceholder('Email').nth(4).fill('recipient3@documenso.com');
+  await page.getByPlaceholder('Name').nth(4).fill('Third Recipient');
+  await page.getByRole('combobox').nth(4).click();
+  await page.getByLabel('Needs to sign').click();
+
+  await page.getByRole('button', { name: 'Continue' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+  await page.getByRole('button', { name: 'Go Back' }).click();
+  await expect(page.getByRole('heading', { name: 'Add Placeholder' })).toBeVisible();
+});