I just found out or exchange servers are migrating to RPC over HTTP. I have 2000+ Outlook/Exchange users. Considering the volume of users, and the existing nuances of their profiles, it would be ...
If Outlook Classic Encryption is not changing, check encryption policy, reset S/MIME, remove Outdated Certificates, remove Conflicting Mail Flow/Transport Rules, etc.
Although Outlook comes with so many options to manage multiple email accounts, it could be a hassle to manage all of them with ease. It could happen due to some default settings that you may not like.