Outlook keeps asking for password? 6 causes and fixes

Outlook keeps asking for your password even after you enter the correct one. This happens on Windows, Mac, Microsoft 365, Gmail and hosted email accounts. Sometimes you can still receive mail but not send. Sometimes nothing stays stable.

If you searched for “Outlook keeps asking for password”, the real cause is usually a broken credential cache, two-factor authentication, old server settings or a Microsoft 365 sign-in flow that is stuck.

Why does Outlook keep asking for your password?

That password prompt does not only appear when the password is wrong. Outlook also shows it when:

• old credentials are stuck locally
• an app password is required
• Microsoft 365 cannot complete sign-in correctly
• IMAP or SMTP is configured incorrectly
• the profile or network connection is damaged

1. First confirm that the password itself is correct

It sounds obvious, but start there anyway. Test the account in webmail:

• Microsoft 365 / Outlook.com: sign in in your browser
• Gmail: test it in Gmail webmail
• Hosting email: test the provider’s webmail

If browser login fails too, then your Outlook issue is not really an Outlook issue. Your password may be wrong, your account may be locked, or an extra security step may be required.

If webmail works but Outlook does not, you already know the real problem sits inside Outlook, the sign-in flow or the local configuration.

2. Think about two-factor authentication and app passwords

If two-factor authentication is enabled, your normal password may no longer work in Outlook, especially with older account types or manual setups.

This comes up often with:

• Gmail with 2FA
• Microsoft 365 with stricter security policies
• hosting email with extra SMTP authentication

Possible fix:

• use an app password if your provider requires one
• remove and re-add the account with the modern login flow

This is especially common after a move to Microsoft 365: users still have an old IMAP profile while the account really needs a Microsoft sign-in flow.

That is a common reason why Outlook keeps asking for a password even when the password is technically correct.

3. Remove old saved credentials

Outlook and Windows often keep old credentials around. If that cache no longer matches reality, Outlook can get stuck repeating the same prompt.

Check:

• Windows Credential Manager
• old Outlook profiles
• stale Microsoft account tokens

Typical pattern:

• password was changed
• Outlook kept using old credentials
• user enters the new password
• Outlook still retries the old token in the background

That makes it look like Outlook “does not remember” the new password when the real problem is the old cached sign-in.

On Windows, Credential Manager is often the first place to inspect. On Mac, an old account profile or keychain item is often involved.

4. Wrong IMAP/SMTP server settings

If you are not using Microsoft 365 but hosting email, I often find wrong server settings.

Check:

• incoming server
• outgoing server
• port numbers
• encryption type (SSL or STARTTLS)
• whether SMTP authentication is enabled

Common combinations:

• IMAP: port 993 with SSL
• SMTP: port 587 with STARTTLS

A wrong port does not always produce a clear error. Outlook may simply keep asking for the password as if that were the real issue.

If you use email on your own domain, always compare the configured servers with the official IMAP/SMTP settings from your provider.

5. Corrupted Outlook profile

If an account was created long ago and changed multiple times since then, the profile itself may be damaged.

Typical signs:

• one account keeps failing while others work
• the new password is always rejected
• Outlook gets stuck on “connecting”
• sending and receiving are unreliable

In that case, creating a clean new profile is often faster than endlessly patching the old one.

For business mailboxes, this is often safer than changing loose settings without a clear overview.

6. Network or security software is blocking Outlook

Sometimes the password is not the real issue. Outlook simply cannot reach the server reliably.

Check:

• does webmail still work?
• is your Wi-Fi unstable?
• is a VPN active?
• is antivirus or firewall software scanning mail traffic?

This is especially suspicious when:

• Outlook fails at home but works elsewhere
• the issue affects both laptop and phone
• the problem started after a network or provider change

When should you stop troubleshooting it yourself?

Trying basic fixes yourself is fine when it is just a recent password change. But stop when:

• you no longer know which profile is the correct one
• multiple mailboxes are mixed together
• old server settings and Microsoft 365 are blended in one setup
• you are worried about losing locally stored mail

At that point it is safer to fix it properly in one go.

Frequently asked questions about Outlook password problems

Why does Outlook keep asking for my password when it is correct?

Because Outlook is often not blocked by the password itself, but by the sign-in token, server setting, account cache or authentication flow.

Should I remove and re-add the account?

Sometimes yes, but not blindly. With a damaged profile or an old IMAP configuration, that is often the fastest fix. If you have locally stored mail, check first what will remain available.

Does this happen often with Microsoft 365?

Yes. I see it regularly after migrations, new security policies, multi-factor authentication or long-lived Outlook profiles.

---

If Outlook keeps asking for your password, I can sort it out in a focused Outlook and email support session. If you are setting up a new device, also read how to set up Outlook on laptop or smartphone. If you use business email on your own domain, this guide about domain email setup also helps.