If your Outlook keeps asking for your Gmail or Google Workspace password, even after enabling POP and creating an App Password, you’re not alone. Thousands of professionals face this frustrating loop — especially after Google enforced 2-Step Verification and enhanced authentication protocols.

In this guide, we’ll cover exactly why this happens and walk you through detailed step-by-step solutions that work for both individual Gmail users and Google Workspace accounts.

? Why Outlook Keeps Asking for Password

Outlook uses older POP/IMAP protocols to connect to email servers.
When Google upgraded its security model (requiring OAuth2 or App Passwords), older Outlook configurations broke because:

• They tried authenticating using your normal Gmail password, not the app password.

• POP access wasn’t fully enabled in Gmail settings or in the Workspace Admin Console.

• The security check blocked “less secure apps.”

• Ports or encryption mismatches existed (e.g., TLS vs SSL).

As a result, Outlook can’t authenticate and keeps prompting for a password.

✅ Step-by-Step Fix Guide

Step 1: Enable POP in Gmail Settings

1. Log in to Gmail (same Google Workspace email).

2. Click the ⚙️ Settings → See all settings → Forwarding and POP/IMAP.

3. Under POP Download:

   • Select Enable POP for all mail (or “Enable POP for mail that arrives from now on”).

   • Choose Keep Gmail’s copy in the Inbox.

4. Click Save Changes.

Step 2: Create an App Password

If you have 2-Step Verification enabled, a normal password won’t work anymore.

1. Visit https://myaccount.google.com/apppasswords

2. Re-enter your password to verify.

3. Choose:

   • App: Mail

   • Device: Windows Computer

4. Click Generate.

5. Copy the 16-character app password (no spaces).

? Important: This password replaces your regular Gmail password when setting up Outlook.

Step 3: Configure Outlook Correctly

Open Outlook → File → Account Settings → Add New Account → Manual Setup / POP or IMAP

Incoming Mail (POP3):

• Server: pop.gmail.com

• Port: 995

• Encryption: SSL/TLS

Outgoing Mail (SMTP):

• Server: smtp.gmail.com

• Port: 465 (SSL) or 587 (STARTTLS)

• Encryption: SSL/TLS

• Requires authentication ✅

• Use same login credentials as incoming mail ✅

Login Information:

• Username: your full email (e.g., user@yourdomain.com)

• Password: the App Password you generated earlier

Uncheck “Require logon using Secure Password Authentication (SPA)” — this causes authentication errors with Gmail.

Step 4: Check Google Workspace Admin Console

If you’re using Google Workspace, the administrator must enable POP access:

1. Go to admin.google.com → Apps → Google Workspace → Gmail → User Settings.

2. Scroll down to POP and IMAP Access.

3. Ensure:

   • ✅ Enable POP access for all users

   • ✅ “Allow users to configure mail clients”

4. Save changes.

5. Wait 15–30 minutes for settings to propagate.

Step 5: Allow Google Security Access

Sometimes Google blocks Outlook’s connection as “suspicious.”

1. Visit https://myaccount.google.com/security-checkup

2. Review any blocked sign-in attempts.

3. Click Yes, that was me / Allow access if Outlook is being blocked.

Then restart Outlook and try again.

Step 6: Clear Old Credentials in Windows

Sometimes cached credentials cause the loop.

1. Go to Control Panel → Credential Manager → Windows Credentials.

2. Look for entries like mail.google.com or your email address.

3. Remove them.

4. Restart Outlook and re-enter the App Password.

Step 7: Test POP Connection

To ensure the POP service is active:

• Visit https://pop.gmail.com
  If it shows a secure certificate and no “Access Denied” message, POP is working.

If blocked, contact your Workspace admin.

⚡ Common Mistakes and Their Fixes

? Expert Tips

• Prefer IMAP over POP if possible — IMAP syncs all folders and is more modern.

• Always use App Passwords for any non-Google client (Outlook, Thunderbird, etc.).

• Avoid using “Less secure app access” — Google has discontinued it since 2022.

• Check Workspace Audit Logs if users still fail to authenticate.

? Summary

Once these are configured correctly, Outlook will connect instantly and stop asking for passwords repeatedly.

? Conclusion

Google’s security changes are meant to protect your data, but they can make traditional clients like Outlook behave unpredictably. The key is to use App Passwords, ensure POP/IMAP is properly enabled, and double-check encryption ports and admin policies.

After following this guide, your Outlook–Google Workspace connection should work flawlessly — no more password prompts!

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