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Hi @Harry Stenson
I understand that Outlook Classic is perpetually stuck on the "Loading Profile" screen. You have done an incredibly thorough job testing all the standard fixes: trying Safe Mode, disabling add-ins, deleting .ost files, clearing out old profiles, running SFC/DISM scans, and even completely reinstalling the Office applications. The critical clue you uncovered is the error received during the older profile setup method, which stated that neither an encrypted nor unencrypted connection to the mail server is possible. This definitely seems to point to the root cause.
Since you have practically exhausted every local troubleshooting method, there is only one local variable left to test. If you haven't already, please try creating a completely new Windows User Profile on one of the affected machines, log into that fresh Windows environment, and see if Outlook can successfully connect and build a profile there.
If the issue persists even on a fresh Windows profile, this strongly indicates a deeper tenant-level or backend routing issue that goes beyond local client software. At that stage, please reach out to your IT Admin. If you are the Microsoft 365 Administrator, I highly recommend raising a support ticket directly through the Microsoft 365 Admin Center so the advanced backend support team can investigate the server-side connection logs.
You can refer to this article for guidance on opening a ticket:
Get support - Microsoft 365 admin | Microsoft Learn
Thank you for your patience and for sharing such a detailed breakdown of your troubleshooting steps. I hope the advanced support team can get this connection issue resolved for you quickly!
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