Windows 11 Office 2021 Pro Outlook eMail Issues

[JamesCRocks]

Hi,

When trying to configure my outlook email account for Outlook on Windows 11, I get these results:

Automatic detection and Microsoft 365:

Manual (which I'd prefer)…

... I get constant requests for my password (which I've checked as working by logging out of and back into outlook.live.com where I can see my mail):

This has been going on for many months, I get the same issue on my laptop. It's a while ago now but I think it may have also affected Outlook on my phone until I switched to BlueMail.

I have 6 other email accounts happily configured in Outlook, all from my web provider… it's just this one from MS that doesn't work.

My Outlook live mail also works on Outlook basic (provided as an app on Windows and available from MS store), BlueMail (both Windows desktop and Android phone) and I can log in normally using my [known] password for various MS services including Outlook Live mail. Just not Outlook as part of MS Office pro 2021.

Any ideas?

James

 

[ChatGPT]

Hi James — thanks for the clear screenshots and description. Short version: this is almost always caused by Outlook trying to connect using basic (IMAP/SMTP) credentials while Microsoft now requires Modern Authentication (OAuth) for Outlook.com/Exchange accounts. That makes IMAP/POP/SMTP sign‑ins either fail or repeatedly prompt for a password in newer Outlook builds unless you use the Exchange/Outlook.com auto-configured connection or an app password. Here’s what to try, in order.
Why this is happening (brief)

• Microsoft has been deprecating Basic Authentication for Exchange/Outlook.com and moving services to Modern Authentication (OAuth). Clients that use IMAP/POP with Basic auth will see repeated prompts or fail.
• Outlook desktop will use Modern Authentication for Outlook.com only when the account is added as an Outlook.com / Exchange profile (automatic configuration). If you configure the same account as IMAP/SMTP in Outlook desktop, Modern Auth is not used and will likely be blocked.
• If you must use IMAP and your Microsoft account has two‑step verification turned on, you must use an app password for IMAP clients that don't support OAuth. Otherwise IMAP/POP may be blocked.
  Step-by-step fixes (do these in order)
• Update Outlook / check build
• Open Outlook → File → Office Account → About Outlook and note the version/build. Outlook 2021 needs a sufficiently recent build for full Outlook.com support. If Office isn't up to date, click Update Options → Update Now. Updating first avoids many compatibility issues.
• Remove the IMAP account and create a new Outlook profile (recommended)
• Close Outlook.
• Open Control Panel → Mail (Microsoft Outlook) → Show Profiles → Add. Give the new profile a name.
• Use Add Account and enter only your full outlook.com address, then let the automatic setup run. When the Microsoft sign-in window appears, complete the OAuth sign-in (this is the Exchange/Outlook.com method that uses Modern Authentication rather than IMAP). This should create an Exchange/Outlook.com type connection instead of IMAP/SMTP.
• Set the new profile as the default and start Outlook.
• Clear stored Windows credentials (common quick fix)
• Open Windows Settings → Search “Credential Manager” → Windows Credentials.
• Remove any entries that reference outlook, microsoftoffice, mso, or your outlook.com address.
• Reboot and open Outlook; when prompted, sign in via the Microsoft/OAuth dialog (not an IMAP password box).
• If you intentionally want to use IMAP (manual) instead of Exchange autoconfig
• Be aware: Outlook desktop does not use OAuth for IMAP/POP, so Basic auth may be blocked by Microsoft. If your account has two-step verification you’ll need to create an app password in your Microsoft Account security settings and use that in Outlook instead of your normal password. If your tenant/organization has blocked app passwords, IMAP might not be allowed at all.
• Run the Outlook troubleshooting tool / Get Help
• Microsoft’s diagnostics for Outlook sign-in problems are now in the Windows Get Help troubleshooters (classic SaRA diagnostics are migrated). Run the Outlook troubleshooters to collect logs and automated checks.
• Other checks
• Temporarily disable third‑party firewall/AV to rule out interference.
• If you use a VPN or proxy, try without it.
• If Autodiscover fails repeatedly, some networks or DNS/firewall rules can block it — try from a different network (phone hotspot) to check.

What I need from you if this still fails

• Tell me the exact Outlook version/build from File → Office Account → About Outlook.
• Confirm whether the account has two-step verification / Authenticator enabled.
• Tell me whether you tried creating a new profile and what error (if any) you now see, or paste the exact message from the credential prompt.

Useful Microsoft docs (quick links referenced above)

• Modern auth and Outlook.com guidance.
• Deprecation of Basic Authentication in Exchange Online.
• Outlook and other apps unable to connect when using Basic auth (recurring prompts) — troubleshooting steps.
• POP/IMAP/SMTP and Modern Auth details (why IMAP may fail).
• How to create and use app passwords for Microsoft accounts.
  If you want, I can walk you step‑by‑step through: (A) checking your Outlook build, (B) creating a new profile and adding the account so it uses Modern Auth, and (C) clearing Credential Manager. Which would you like to try first?