We have 2019 servers running a RDP environment for many of our clients. 10 servers are being used as traditional workstations. The others are brokers, Fileservers, Web, App, SQL, ETC.

Question: Is anyone else having a constant battle with O365 e3 and e5 users? Outlook randomly stops opening, Profiles lose connection to microsoft. Users cant sign in. We get 1001 errors. If we run a repair and reboot it fixes it sometimes until the next update, Ive seen some other forums talk about deleting and replacing OneAUTH and other folders which fixed 1001 errors but im surprised there hasnt been more of a permenant fix. We have noticed updates cause some of the problems. Any suggestions are more than welcome. Thank you guys!

10 Spice ups

I found that disabling the UDP property for RDP cured my issues.

Users were having to disconnect and reconnect to re-establish their session prior to the fix

Do you use Cached Mode?

Previously, MS did not support using cached mode with RDP.

Now it is! Plan and configure Cached Exchange Mode in Outlook 2016 for Windows - Outlook | Microsoft Learn

But I disable it in RDP projects anyway, as this works more stable.

Where are the profiles? Do not put the OST (only exist if Cached Mode enabled) or PST files (PST files are a bad idea anyway) on network shares.

Our profiles are being stored for each use as a profile disk on the file server being mapped by broker. We are running O365 but ill take a look at that today. Thank you!

Typical slow disk performance issues when the profiles are on another system

Found out that Microsoft released an update on 8/11 and 8/12 also on the 30th and 31st that was directly causing login issues from the desktop app. We fixed some local machines and oddly enough then the profiles worked on the RDP environment. They are suppose to release a patch later.

Always try to access your Outlook 365 account without caching , It will improve your Outlook performance.