Classic outlook - Teams add-in not loading

We recently had a partner experience an issue that is causing the teams add-in feature to not load properly in classic outlook when creating a new meeting. For some background info, we are using a Virtual environment within remote desktop running windows 11. Our servers are provided by AWS. The issue only began as recently as December, as far as we can ascertain with the customers information. I have noticed this issue occurs with numerous partners but is inconsistent, as some load and others do not. I followed troubleshooting steps such as an uninstall/reinstall, verifying the load behavior in the registry was set to 3, and tried to re-register the related teams.addinLoader.dll. A colleague did implement a script to the environment task scheduler that will run every time outlook is launched to re-install that add-in as a break fix, but this still requires closing outlook and reloading it to work. I was curious if anyone else had encountered this within remote desktop with classic outlook, and if they had any success in fixing it. The easiest thing, obviously, is moving over to new outlook since teams' integration is native, but we have some that prefer classic. Though, with it being retired in 2029 it may be worth starting the move away while in a remote environment.