Outlook keeps prompting you for your Gmail password during SMTP setup

blog.payperitem.com, April 24, 2025

1. Enable IMAP/SMTP in Gmail Settings

Log in to Gmail.
Go to ⚙️ Settings > See all settings > Forwarding and POP/IMAP
Enable IMAP and/or POP, and make sure SMTP is allowed (default behavior with IMAP).

2. Use App Password (if 2-Step Verification is enabled)

If you use 2-Step Verification in Gmail:

Go to: https://myaccount.google.com/apppasswords
Generate an App Password for Outlook.
Use that password in Outlook instead of your normal Gmail password.

Without this, Gmail will reject access attempts even if the password is correct.

3. SMTP & IMAP Settings for Gmail

Make sure these settings are correct in Outlook:

SMTP Server: smtp.gmail.com
SMTP Port: 465 (SSL) or 587 (STARTTLS)
Encryption: SSL/TLS or STARTTLS
IMAP Server: imap.gmail.com
IMAP Port: 993
Username: your full Gmail email address
Password: your Gmail App Password

4. Allow Less Secure Apps (Only if no 2FA)

If you’re not using 2FA, enable:

https://www.google.com/settings/security/lesssecureapps

⚠️ Google is phasing this out, so using 2FA + App Password is more reliable.

5. Check Captcha Unlock

Sometimes Google blocks access temporarily.

Unlock: https://accounts.google.com/DisplayUnlockCaptcha
Sign in and confirm.

6. Firewall/Antivirus Interference

Check if your firewall or antivirus is:

Blocking Outlook from accessing Gmail’s SMTP server.
Temporarily disable them and test.

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