Why Are Users Constantly Being Prompted to Re-Authenticate in M365?
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MoonlitGadget92
Hey everyone! I've been hearing from some users who keep getting asked to re-authenticate while using M365 services like Teams, OneDrive, and Outlook. This issue isn't affecting everyone, and I haven't spotted any particular trend. Is there anything I can try before I reach out to Microsoft Support for help?
Answers
Have you checked the sign-in logs? They can reveal why users are being prompted for MFA. It's worth looking into any Conditional Access policies that might be going off too.
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We're in GCCH, and the rollout of Copilot has triggered similar issues for some users. They can log in fine, but an empty sign-in window pops up and fails authentication. We found that removing Copilot from their profile resolves it for now, and we're working on removing it company-wide.
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Check if any users are classified as risky in Entra; that can definitely cause issues too.
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It might help to have them update their password, either through SSPR or an admin. Sometimes that clears things up.
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Don't forget to take a look at your Microsoft 365 Conditional Access Policies. Recently, they introduced a rule that triggers re-authentication for logins considered 'suspicious,' like unfamiliar IPs or locations.
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I had to re-authenticate Teams on mobile multiple times over the weekend, like 5-6 times! That 30-day setting didn’t seem to help at all.
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Does this happen when they change their passwords? Also, what MFA provider are you utilizing?
MoonlitGadget92: Unfortunately, that's not the issue. We use the Authenticator app for MFA.
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Have they made sure to register both their mobile app and their mobile number? They might be skipping one of those steps and getting prompted to finish registration.
MoonlitGadget92: They’re not seeing prompts to register again; it’s just re-auth and confirmation. Some users have both their app and number registered, but most only have the app.
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What antivirus are your users running? That can sometimes interfere with authentication processes.
MoonlitGadget92: We’re using Crowdstrike Falcon for AV.
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I've dealt with a similar issue and enabled modern authentication using a registry key. It’s been about two weeks since then, and so far, so good! Might be worth trying if you haven’t already.
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From my experience, this issue mostly arises on Windows 10 and LTSC systems. Have you noticed if it’s specific to those OS versions?
MoonlitGadget92: I wish it was just that! The users experiencing this problem are on a mix of Windows 10 and 11.
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MoonlitGadget92: Last I checked, the logs just mentioned that the sign-in was interrupted. I don’t recall the Conditional Access specifics either. I'm asking users to flag it when it happens, but currently, I have three different tickets opened with similar complaints.