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--- fix_constant_sign-in_prompt_for_microsoft [2026/02/15 22:17] – created artmelson09
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-[[https://www.youtube.com/shorts/v0gEt30jQkc|external page]]Content
-(Image: [[https://cdn-dfknk.nitrocdn.com/BMGKLORDabDBCUPuWOjTkLVrPSWteURh/assets/images/optimized/rev-47e4c7f/www.stellarinfo.co.in/blog/wp-content/uploads/2023/09/How-To-Fix-Outlook-2016-Search-Problems-407x247.jpg|https://cdn-dfknk.nitrocdn.com/BMGKLORDabDBCUPuWOjTkLVrPSWteURh/assets/images/optimized/rev-47e4c7f/www.stellarinfo.co.in/blog/wp-content/uploads/2023/09/How-To-Fix-Outlook-2016-Search-Problems-407x247.jpg]])
-Right now we have it set to prompt when a user is not on any of our corporate networks or they are using a mobile device. To locate and view the registry setting for Anonymous Authentication in the Outlook profile, follow these steps. This issue can occur if the Logon network security setting on the Security tab of the Microsoft Exchange dialog box is set to a value other than Anonymous Authentication. Today was the first time in about 2 months that I had the issue. It happened right before lunch, locked my machine, went out for lunch, came back, and logged in, this time successfully.
-Additional resources
-Please help can't afford a new computer if I throw this one against the wall. Yeap, you describe it exactly and unfortunately we still don’t have an answer. Closed the window without entering anything and Outlook returned to ‘Connected to Exchange’. Office 2016 is already Modern Authentication aware so APP passwords are not required.
-(Image: [[https://i.ytimg.com/vi/0NfNugXoVyY/hq720.jpg?sqp=-oaymwEhCK4FEIIDSFryq4qpAxMIARUAAAAAGAElAADIQj0AgKJD&rs=AOn4CLCW7PGXm_H7_sALyVHcHe83DUQDag|https://i.ytimg.com/vi/0NfNugXoVyY/hq720.jpg?sqp=-oaymwEhCK4FEIIDSFryq4qpAxMIARUAAAAAGAElAADIQj0AgKJD&rs=AOn4CLCW7PGXm_H7_sALyVHcHe83DUQDag]])
-Microsoft Office 365 Endless Authentication Loop Issue
-I cannot find the phone number again to contact MS Office support (eventually they were helpful, but only after insisting they help!), I'm in the Netherlands so if someone has a phone number, I'd love to get it again.Before you access it, back up the registry for restoration in case problems occur.On the off chance that none of these things solve this issue for you, please contact our support team atClear the Windows Credential manager or recreate the users Outlook profile.The connection to Microsoft Exchange is unavailable.We checked with Word that the account was connected–it was and the we opened Outlook and it immediately connected.Office 2016 is already Modern Authentication aware so APP passwords are not required.
-In each case the fix has either been one of the above items or a combination of them. There doesn’t appear to be any pattern to the issue occurring or the problem being limited to any specific computer or user. By chatting and providing personal info, you understand and agree to our Terms of [[https://lab.nltvc.com/jeromeb8725341/9214999/-/issues/1|lab.nltvc.com explains]] Service and Privacy Policy. I disabled the Zoom and Adobe PDF plugins and it stopped prompting me immediately. My client’s Outlook will only continuously ask for the password after MFA is enforced and Office.com has been logged in. It would be nice if it distinguished between your password and the app password.
-Outlook stuck in an MFA loop
-(Image: [[https://www.theknowledgeacademy.com/_files/images/Microsoft_Outlook_Issues.png|https://www.theknowledgeacademy.com/_files/images/Microsoft_Outlook_Issues.png]])
-The [[https://demo.safecircle.family/read-blog/35545_12-tips-to-fix-outlook-send-and-receive-error-2025.html|Fix Outlook Not Opening After Windows Update]] user had Office 2015 and Office 2016 credentials and Teams credentials that we deleted. We checked with Word that the account was connected–it was and the we opened Outlook and it immediately connected. We too have been seeing this more and more, all W10 on O365, although we use Okta as our MFA. Have looked all over and people have all sorts of possible solutions, but nothing we found to resolve the issue and get a new issue daily  and just keep going through until it eventually works. I’ve seen this happen when the time and or date is wrong on the machine. It’s not caused by an out of sync MFA prompt as I have personally looked at a number of cases with the user as stepped through it.
-Outlook 365 Password Prompt Issue on Windows Desktop
-So not doing anything at all even seems to work. Which to me sounds [[https://code.swecha.org/stacisalcido2/geoffrey1990/-/issues/1|Fix Outlook and Office365 Sync Issues]] like the issue is service side, not client side. Problem doesn’t just happen on PC’s connected to the internal network, but can happen when a laptop is remote and connected  via external wifi or mobile hotspot.