Using Classic Outlook on Windows for personal email, calendar, and contact management
We had this problem about 2 months ago for a couple of weeks and then it stopped for us on it's own but last week it's come back however we have changed the version and release of Office on our RDS servers without success BUT we have 6 RDS servers, 4 of them are covered by FSLOGIX and a broker
and 2 are independent using local profiles and the one's using local profiles never had ANY issues so certainly for us it looks all down to FSLOGIX so i disabled the ability to roam identities, ran GPUPDATES and then rebooted all and straight away all worked fine for the past 6 days. We'd had a few residual people having to log back in when opening Outlook but then once logged in they've been fine.
It seems different setups and different people may have different issues but in a 2022 RDS scenario with FSLOGIX profiles and Office 365 app for business (or Enterprise - any version) then this has fixed it for us (at least for now)
I did also run the 2 commands to re-register these packages but i didn't run these on the non-FSLOGIX servers and again they've had no issues so i think we can discount these as being the fix for us (unless they fixed something that the FSLOGIX servers had broken)
Add-AppxPackage -Register "$env:windir\SystemApps\Microsoft.AAD.BrokerPlugin_cw5n1h2txyewy\Appxmanifest.xml" -DisableDevelopmentMode -ForceApplicationShutdown
Add-AppxPackage -Register "$env:windir\SystemApps\Microsoft.Windows.CloudExperienceHost_cw5n1h2txyewy\Appxmanifest.xml" -DisableDevelopmentMode -ForceApplicationShutdown