Outlook fix · classic (Windows)
Outlook keeps asking for your password and won't accept it
If classic Outlook keeps popping the password box even after you type the right password, the desktop app is almost always holding a stale, cached credential. The reliable fix is to remove Outlook's saved logins from Windows Credential Manager and let it re-authenticate cleanly. Here's how, step by step. Rated 4.9 on Google.
- ● Stale saved credential
- ● Credential Manager reset
- ● We'll fix it remotely
First, one quick check
Does the password work on the web?
Before changing anything, confirm the password itself is right. Open a browser and sign in to Outlook on the web (outlook.office.com for a work or Microsoft 365 account, or outlook.com for a personal account) with the same email and password.
- If the web login works but the desktop app keeps prompting, the password is fine, the app is holding a stale saved credential. The fix below clears it.
- If the web login also fails, your password has genuinely changed or expired. Reset it with your provider first, then come back and re-enter it in Outlook.
This one check saves you chasing the wrong problem.
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The fix
Clear the stale credential in Credential Manager
These steps are for classic Outlook on Windows. Work through them in order.
- Close Outlook completely.
- Open Credential Manager. Press the Windows key, type Credential Manager, open it, and click Windows Credentials.
- Remove the Outlook logins. Under Generic Credentials, look for any entry starting with MicrosoftOffice, Outlook, or your email address. Expand each one and click Remove. (Deleting these only clears saved passwords, it doesn't touch your email.)
- Reopen Outlook and, when prompted, sign in once. Tick Remember my credentials (or Keep me signed in) so it saves cleanly this time.
- Turn off the constant prompt (older setups only). If it still nags and you're on a legacy Exchange account, go to File > Account Settings > Account Settings, double-click your account, click More Settings > Security, and untick Always prompt for logon credentials. On modern Microsoft 365 accounts this tickbox is usually greyed out or missing because sign-in is handled by modern authentication, so don't worry if you can't change it.
The setting that fixes most of these:
- Update Office. Go to File > Office Account > Update Options > Update Now. Newer builds use modern (OAuth) sign-in, which older versions can't do, and that mismatch is one of the most common causes of the loop. Updating, then re-adding the account, resolves it in most cases.
- Two-factor authentication? With a modern, up-to-date Outlook you sign in with your normal password and approve the prompt on your phone. App passwords are now retired for Outlook (personal accounts from 2024, work and school accounts from 2025), so if an old guide tells you to create one, ignore it and update Office instead so it can sign in the modern way.
If it still loops after all that, a fresh Outlook profile is the last resort (Control Panel > Mail > Show Profiles > Add). Set the new profile as default. For Microsoft 365, Outlook.com and other IMAP or Exchange accounts your mail re-downloads from the server, so nothing is lost. If it's a POP account, older mail may only exist locally in your data file, so back up your .pst first. It's fiddly either way, and it's the point where most people hand it to us.
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// GOOD QUESTIONS
Frequently asked
Why does Outlook keep asking for my password when I've typed it correctly?
Classic Outlook is holding a stale, cached credential that no longer matches your account. Even the right password gets rejected because the app never gets past the old saved one. Removing Outlook's entries from Windows Credential Manager and signing in again clears it.
How do I stop Outlook asking for a password every time?
Remove the Outlook and MicrosoftOffice entries in Credential Manager > Windows Credentials, reopen Outlook and sign in ticking Remember my credentials, then update Office so it uses modern sign-in. On older legacy Exchange accounts you can also untick Always prompt for logon credentials under your account's More Settings > Security, though that tickbox is greyed out on modern Microsoft 365 accounts.
How do I check if my password is actually right?
Sign in to Outlook on the web (outlook.office.com for a work or 365 account, or outlook.com for a personal one) with the same email and password. If the web login works but the desktop app keeps prompting, the password is fine and the app has a stale credential. If the web login also fails, reset your password with your provider first.
Do I need an app password for Outlook?
No. App passwords have been retired for Outlook, for personal Microsoft accounts since 2024 and for work and school accounts through 2025, because Microsoft moved to modern authentication. With an up-to-date Outlook you sign in with your normal password and approve the two-factor prompt on your phone. If an old guide tells you to create an app password, update Office instead so it can sign in the modern way.
Will removing credentials or making a new profile delete my emails?
Removing entries in Credential Manager only clears saved passwords, not mail. Creating a fresh Outlook profile re-downloads your email from the server for Microsoft 365, Outlook.com and other IMAP or Exchange accounts, so nothing is lost. If you're on a POP account, older mail may only be stored locally, so back up your .pst data file first, which is why many people ask us to do it.
Can you fix the Outlook password loop remotely?
Yes. Call 365 Techies on 01202 775566 and we'll clear the stale credential and get you back into email remotely over Splashtop SOS, usually within minutes. We phone first, you watch every step, and access ends when we're done. We're Bournemouth-based, same-day, Windows and Android specialists.
Password loop driving you mad? We'll break it
A stuck password prompt can lock you out of email for hours. Call 365 Techies on 01202 775566 and we'll clear the stale credential and get you back in remotely over Splashtop SOS, usually within minutes. We phone first, you watch the whole time, access ends when we finish. Same-day, Bournemouth-based, 4.9 on Google.
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