Hi @Zacharias Embaxter ,
If permitted by your organization’s sign-in requirements, you may also test the following registry value with 1 or 2 for one affected user:
HKEY_CURRENT_USER\Software\Policies\Microsoft\office\16.0\common\signin
SignInOptions = 3 (DWORD)
Please test each value separately, restart Outlook, and check whether the behavior changes. Since this value is managed through Group Policy, your administrator may need to make the temporary change. If there is no difference, please restore the original value of 3.
Disclaimer: Generally, modifying registry subkeys or work group is intended for advanced users, administrators, and IT Professionals. It can help fix some problems, however, serious problems might occur if you modify the registry incorrectly. Therefore, make sure that you follow these steps carefully. For further protection, back up the registry before you modify it. Then, you can restore the registry if a problem occurs. For more information about how to back up and restore the registry, click How to back up and restore the registry in Windows to view the article.
Since this is an enterprise environment, could you also confirm whether the issue affects all users who receive the same Group Policy settings, or only specific users or devices?
Additionally, please try starting Outlook in Safe Mode by pressing Windows key + R, entering the following command, and selecting OK: outlook.exe /safe
Safe Mode starts Outlook without most add-ins and custom settings. If the message does not appear in Safe Mode, an add-in or Outlook customization may be contributing to the issue. Open Outlook in safe mode
If the issue continues, please try creating a new Outlook profile by following the steps in this official Microsoft Support article: Create a profile in classic Outlook for Windows. This will help determine whether the issue is related to the existing Outlook profile.
Feel free to share the requested details when convenient. I look forward to hearing from you.