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

Jennifer Blamey 2025-12-04 08:23:37 +08:00
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Content<br>
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
This is now the 2nd machine that presents the same issue. I have a valid MS 365 subscription that includes 5 device licenses. On the main machine where I have been using the suite, now my account is deactivated and if I try to authenticate, it looks like it works but then get the "Fix", "Authenticate", "Activate" or "Resolve" buttons, all of which do nothing. I checked my MS account info page, subscription is fine. I had this exact issue on another machine, that after 2.5 hours on the phone with MS support (via Zoom), the solution was to uninstall MS Office 365 and reinstall it.
Microsoft Office 365 Endless Authentication Loop Issue
We’ve got a support case opened with Microsoft on this one but it’s been open for about 3 months.There doesn’t appear to be any pattern to the issue occurring or the problem being limited to any specific computer or user.We are looking at using conditional access policies where a user with a Domain joined PC is not prompted for MFA.It happened right before lunch, locked my machine, went out for lunch, came back, and logged in, this time successfully.I checked my MS account info page, subscription is fine.When we opened the old, existing profile it didn’t ask for ANY authentication, it just started working.I had this exact issue on another machine, that after 2.5 hours on the phone with MS support (via Zoom), the solution was to uninstall MS Office 365 and reinstall it.The user could use the Windows mail and calendar apps but Outlook wouldn’t connect and kept prompting for a password.I disabled the Zoom and Adobe PDF plugins and it stopped prompting me immediately.
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. [Outlook sync help from FixTechGuide](https://gitlab.innive.com/jacquelinerech/7090resolve-outlook-not-sending-emails-fast/-/issues/3) 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
Close and open your web browser again and go into [Outlook profile repair and recovery steps](https://indiancrafts79.com/repair-an-office-application-16/) SuiteFiles. You will most likely need to enter your Microsoft 365 credentials again so ensure you tick any box that says remember my credentials but it should now work for all future documents you open and not require your credentials. Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support. I regret that you are experiencing issues with your Microsoft installation.
Outlook 365 Password Prompt Issue on Windows Desktop
You can reply to reactivate the question if you decide you want to continue. Let's [connection status shows Disconnected](https://git.epochteca.com/rory2409242378) start by answering a few simple questions to understand the problem. We have been experiencing the exact same issue for months now. I experience the issue myself as well, every once in a while. On the off chance that none of these things solve this issue for you, please contact our support team at