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 GoogleFamily-run since 1995 · no fix, no feeFirst, 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.
// WINDOWS PCS ONLY
We do not support Outlook on Apple Macs, iPads or iPhones. Apple does not allow our remote-support tool to take control of an iPad or iPhone (an Apple restriction), and our remote support covers Windows PCs only. On an Apple device, Microsoft’s own Outlook help is the place to start.
// FIX IT WITH ME · STEP BY STEP
Fix it with me, one step at a time
The steps from this guide, one at a time, in the order that fixes the most cases fastest. Tell it what happened and it shows the next step. Nothing here leaves your device.Last reviewed 6 October 2026
-
01Confirm the password works on the web
Sign in to Outlook on the web with the same email and password. If that works but the desktop app keeps prompting, the app has a stale saved credential.
Is it working now? -
02Close Outlook and open Credential Manager
Close Outlook completely, press the Windows key, type Credential Manager, open it, and click Windows Credentials.
Is it working now? -
03Remove the stale Outlook logins
Under Generic Credentials, expand and Remove any entry starting with MicrosoftOffice, Outlook, or your email address. This only clears saved passwords, not email.
Is it working now? -
04Reopen Outlook and sign in again
Reopen Outlook, sign in once when prompted, and tick Remember my credentials so it saves cleanly.
Is it working now? -
05Update Office and, only if needed, make a new profile
Update Office (File > Office Account > Update Options > Update Now) so it uses modern OAuth sign-in, then re-add the account. On older legacy Exchange accounts you can untick Always prompt for logon credentials under More Settings > Security, though it is greyed out on modern 365 accounts. A new profile is a last resort; back up your .pst first if you're on a POP account.
Is it working now?
Rather have it done for you? Remote help from £20, or in person across Bournemouth, Christchurch, Poole, Ringwood and the New Forest, with no call-out fee.
Sorted{mins}. Nice work.
Send yourself a test email to be sure it has stuck.
Still not working after all five steps? That is a remote job.
With your permission we connect to your screen and sort it in one session. Usually the same day, remote help from £20, and no fix, no fee.
Outlook keeps asking for your password and won't accept it - the fix order (365techies.co.uk/outlook-keeps-asking-for-password/) 1. Confirm the password works on the web: Sign in to Outlook on the web with the same email and password. If that works but the desktop app keeps prompting, the app has a stale saved credential. 2. Close Outlook and open Credential Manager: Close Outlook completely, press the Windows key, type Credential Manager, open it, and click Windows Credentials. 3. Remove the stale Outlook logins: Under Generic Credentials, expand and Remove any entry starting with MicrosoftOffice, Outlook, or your email address. This only clears saved passwords, not email. 4. Reopen Outlook and sign in again: Reopen Outlook, sign in once when prompted, and tick Remember my credentials so it saves cleanly. 5. Update Office and, only if needed, make a new profile: Update Office (File > Office Account > Update Options > Update Now) so it uses modern OAuth sign-in, then re-add the account. On older legacy Exchange accounts you can untick Always prompt for logon credentials under More Settings > Security, though it is greyed out on modern 365 accounts. A new profile is a last resort; back up your.pst first if you're on a POP account. Still stuck? 365 Techies fix it remotely: 01202 775566 - https://365techies.co.uk/remote-support/// NEED THIS FIXED RIGHT NOW?
Skip the DIY — call 01202 775566 and we can be looking at your screen within minutes. You watch everything we do, and most problems on this page are fixed in one short remote session. (Mon–Fri, 9am–5pm.)
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.
Two more things that often help:
- 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 a common cause of the loop. Updating, then re-adding the account, often resolves it.
- Two-factor authentication? With a modern, up-to-date Outlook you sign in with your normal password and approve the prompt on your phone. For a Microsoft account (Outlook.com, Hotmail or Microsoft 365) you don't need an app password: update Office so it can sign in the modern way. Some other providers are different: a Virgin Media address needs a Virgin Media Mail app password, made in the My Virgin Media app, and making a new one stops the old one working on every device.
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 a sensible point to hand it to us.
FAMILY-RUN SINCE 1995 · ★ 4.9 ON GOOGLE · 200+ COMPUTERS UNDER OUR CARE · NO FIX, NO FEE · SAME-DAY REMOTE SUPPORT
// 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?
Not for a Microsoft account: Outlook.com, Hotmail and Microsoft 365 addresses sign in through Microsoft's own sign-in window instead. Some other providers do need one: a Virgin Media address needs a Virgin Media Mail app password, made in the My Virgin Media app, and making a new one stops the old one working on every device. With an up-to-date Outlook you sign in with your normal password and approve the two-factor prompt on your phone. For a Microsoft account, 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.
// Still stuck?
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.
We’ll fix it with you
- Checking the problem is free
- Fixes from £20, agreed before we start
- We phone first, and you watch every step
Stop it happening again
- A full service every six weeks, written up
- Every program kept up to date
- Unlimited remote help when you need it
Plans from £18.25 a month per computer · cancel any time
Mon–Fri 9–5 · family-run since 1995 · rated 4.9 on GoogleBook a remote fix →