Guides / Outlook keeps asking for a password: how to stop the prompts

Last reviewed 5 Oct 2026

Outlook keeps asking for a password: how to stop the prompts

Repeated Outlook password prompts on Microsoft 365 are usually tokens, cached credentials or Conditional Access — not a mailbox outage.

The user types the password. Outlook says thanks, then asks again ten minutes later. Or the box flashes up and disappears before anyone can type into it. This ticket used to be about saved passwords. On Microsoft 365 today it is about tokens: the sign-in broker on Windows hands Outlook a token, and something is stopping that token from being issued, saved or accepted.

First: is it Microsoft?

Open Outlook on the web in a private window and sign in as the same user. If it loads mail, Exchange Online and the account are fine. If it fails with an error, read the error; a sign-in error code (it starts with AADSTS) tells you far more than the desktop prompt. Check the Outlook status page and, if you are an admin, Service health in the Microsoft 365 admin centre.

User-level fixes, in order

1. Did the password change recently? A new password on one device and the old one saved on a phone can lock the account repeatedly. Update or remove the account on the phone first.
2. Sign out of Office properly. In Outlook: File → Office Account → Sign out. Close every Office app, including Teams, then open Outlook and sign in once.
3. Clear old saved credentials. Open Credential Manager → Windows Credentials. Remove entries that start with MicrosoftOffice and any that mention outlook.office365.com. Restart Outlook.
4. Check "Access work or school". Windows Settings → Accounts → Access work or school. A stale or duplicate work account here confuses the broker. Do not disconnect a device your IT team joined; ask them first.
5. New Outlook profile. Control Panel → Mail → Show Profiles → Add. If the new profile is quiet, the old one was carrying stale settings.
6. Update Office. File → Office Account → Update Options → Update Now. Old builds have had genuine prompt-loop bugs that a later build fixed.

Admin-level checks (Microsoft 365 / Entra)

• Entra sign-in logs. In the Microsoft Entra admin centre, open the user's sign-ins and filter to the Outlook application. Look at both interactive and non-interactive sign-ins. Repeated failures with a clear code (password expired, MFA required, blocked by Conditional Access) are your answer.
• Conditional Access sign-in frequency. A policy that forces re-authentication every hour will feel exactly like a broken Outlook. Use the What If tool to see which policies apply to this user on this device.
• Device state. On the PC, run dsregcmd /status. On an Entra-joined or hybrid-joined machine you want AzureAdPrt : YES. If the device has no primary refresh token, single sign-on to Office cannot work and Outlook will keep asking.
• The Windows sign-in broker. A damaged broker package under %LOCALAPPDATA%PackagesMicrosoft.AAD.BrokerPlugin_cw5n1h2txyewy is a known cause of prompt loops. Back it up and follow Microsoft's documented re-registration steps rather than deleting folders at random.
• Legacy registry tweaks. Old forum fixes that force Office away from the modern sign-in broker are not supported on current builds. If someone applied them years ago, remove them.
• Licence and mailbox. Confirm the user still has an Exchange Online licence and the mailbox exists. A removed licence produces odd prompts before it produces a clean error.

When to escalate

Escalate to Microsoft when Outlook on the web also fails for several users at once, the sign-in logs show service-side errors rather than policy failures, and Service health mentions authentication or Exchange. Escalate internally to whoever owns Conditional Access when the logs show a policy is doing it; that is a design decision, not a fault. If the user is seeing prompts they did not trigger, treat it as a possible compromised password: reset it and revoke sessions.

Related status pages

• Outlook
• Microsoft Entra ID
• Microsoft 365

Related guides

• Microsoft 365 sign-in loop or 'More information required'
• Outlook disconnected or not syncing: is it Microsoft or you?
• Microsoft Authenticator not getting notifications: fixes

FAQ

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

On Microsoft 365, Outlook uses a sign-in token, not the saved password. If the token cannot be issued or saved, because of stale cached credentials, a damaged sign-in broker, or a Conditional Access policy, Outlook keeps prompting even though the password is right.

Is Outlook asking for a password a sign of an outage?

Rarely. If Outlook on the web works for the same account, Exchange Online is up. Widespread prompts across many users at the same minute are worth checking against the official Microsoft 365 status page and Service health.

Should I delete everything in Credential Manager?

No. Remove only the Microsoft Office and Outlook entries for the affected account. Clearing everything can sign the user out of unrelated apps and VPNs.

Will a new Outlook profile delete my email?

Not on Microsoft 365. Mail lives in Exchange Online; a new profile downloads it again. It can take a while on a large mailbox, and local-only PST files need to be re-attached.