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Add Outlook continually prompts for password when you try to connect to Microsoft 365 Outlook Microsoft Learn

Connie Sun 2025-12-29 13:34:23 +00:00
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Content<br>
Also, at the time, that user did not have MFA turned on. In the instances that this occurs the effected user is not new to MFA but has been running it for at least months. The problem appears to randomly affect users (I’ve had it affect myself once too), and the only solution appears to one of (or a combination of) the options in the OP. Out of 140 staff the problem seems to occur once every 2-3 weeks on average.
Additional resources
The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action. Create your account and connect with a world of communities. 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.
Microsoft Office 365 Endless Authentication Loop Issue
Microsoft Outlook 2016 and some recent builds of Outlook 2013 are not affected by this issue.We have been experiencing the exact same issue for months now.If this box is greyed out or disabled then you need to reset the Windows Credential Manager first.We had the issue where Outlook 2016 kept prompting for a password for an Office 365 user whose laptop was connected to their Office 365 account using Windows 10 Pro.The repeated issue logging in started after I enabled the modern authentication in the Office 365 administration panel.This is now the 2nd machine that presents the same issue.
When we opened the old, existing profile it didn’t ask for ANY authentication, it just started working. Modifying the Outlook profile by using the "Profiles" registry path is not supported and may cause your Outlook profile to be in an unsupported state. [disable faulty add-ins in Outlook](http://boiler.ttoslinux.org/williepearson5/2031943/-/issues/1) Serious problems might occur if you modify the registry incorrectly. Before you access it, back up the registry for restoration in case problems occur. We are looking at using conditional access policies where a user with a Domain joined PC is not prompted for MFA.
Outlook stuck in an MFA loop
I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and [Outlook sync help from FixTechGuide](http://boiler.ttoslinux.org/lena57w3378606/carlota1991/-/issues/4) tablet. So figuring that was the same issue here, I did the same thing. I'm also getting Error 29, which the MS support rep couldn't explain to me. I even tried disabling my anti -virus while authenticating, that didn't work.
Outlook 365 Password Prompt Issue on Windows Desktop
So not doing anything at all even seems to work. Which to me sounds [credential loop in Microsoft 365](https://campusbiasharaclub.com/read-blog/564_long-delay-to-receiving-mail-on-outlook-365-windows-11-forum.html) 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.