Outlook keeps asking for my password

The password box appearing repeatedly means the server rejected the login, or Outlook never reached the server. Don't keep clicking OK: every failed attempt counts towards a block on your connection. Cancel the box and work through these checks.

1. Test the password in webmail

1. Go to https://yourdomain/webmail.
2. Log in with the full email address and the password you're typing into Outlook.

• Webmail rejects it: the password is wrong or was changed. Reset it in your control panel (see How to reset or change an email account password), then enter the new one in Outlook.
• Webmail accepts it: the password is right. Continue.
• Webmail won't load at all: go to step 2.

2. Check whether your connection is blocked

Outlook retries a wrong password many times a minute. After enough failures, the server blocks your connection's IP address. Once blocked, Outlook can't reach the server at all, and keeps asking for the password even though it's correct.

Signs: webmail, your website and the control panel all fail from your connection, but work on a phone using mobile data.

Fix: open a support ticket with your public IP address (search "what is my IP" from the affected connection). Fix the wrong password first, or the block returns. See My website works for others but not for me.

3. Check the account settings in Outlook

A mismatch between port and security type produces the same password prompt as a wrong password.

Classic Outlook: File → Account Settings → Account Settings, select the account, click Change, then More Settings → Advanced and Outgoing Server tabs.

New Outlook: Settings → Accounts, then select the account and choose to manage it.

Compare with:

Common mistakes: 993 with STARTTLS, 465 with STARTTLS, 587 with SSL/TLS, and SPA ticked. Full details in Email server settings: IMAP, POP3 and SMTP.

4. Clear saved passwords in Windows

Windows keeps its own copy of the password, and Outlook may use the stale one.

1. Close Outlook.
2. Open Credential Manager from the Start menu.
3. Click Windows Credentials.
4. Remove every entry mentioning your email address, mail.yourdomain, or MicrosoftOffice.
5. Open Outlook and enter the password when asked. Tick Remember my credentials.

On a Mac, open Keychain Access, search for your mail server name and delete the entries, then reopen Outlook.

5. Certificate prompt instead of password prompt?

If the box says the server's security certificate doesn't match or can't be verified, the server name in Outlook doesn't match the certificate. Use mail.yourdomain.co.za as the server name, not an IP address or a different domain. If the warning continues, open a support ticket with a screenshot.

6. Outlook is trying to use the wrong kind of account

New Outlook and recent Outlook 365 versions try Exchange or Microsoft 365 settings first. Your mailbox is a standard IMAP account.

• When adding the account, choose Advanced options → Let me set up my account manually → IMAP, and enter the settings from step 3.
• If Outlook keeps switching to Exchange, remove the account and add it again with manual settings.

7. Create a new Outlook profile

A damaged profile keeps asking regardless of settings.

1. Close Outlook.
2. Open Control Panel → Mail (Microsoft Outlook) → Show Profiles.
3. Click Add, name it, and set up the account with the manual IMAP settings.
4. Under When starting Microsoft Outlook, use this profile, choose the new one.
5. Open Outlook. Once it works, you can remove the old profile.

With IMAP, your email is on the server and reappears in the new profile. Local folders in a .pst file need to be reattached under File → Open & Export → Open Outlook Data File.

8. Antivirus or security software

Some antivirus products scan email by sitting between Outlook and the server. This can break the secure connection and produce password prompts. Temporarily disable the email-scanning feature (not the whole antivirus) and test. If it fixes it, add an exception for your mail server or turn off email scanning; Outlook's own connection is already encrypted.

Still stuck?

Open a support ticket and include:

• The email address.
• Whether webmail accepts the password.
• Outlook version: classic or New Outlook, Windows or Mac.
• The incoming and outgoing server, port and encryption settings you have entered.
• The exact wording of the prompt or any error, with a screenshot.
• Whether other devices with this mailbox work.
• Your public IP address (search "what is my IP") from the connection Outlook runs on.
• When it started, and whether the password was changed around then.