Hi @lukel_3991, I think we have two different issues that are happening here. The first one it seems to not be synchronizing over the extensions. What version of PowerShell do you have installed on your remote server and the otter server? The PowerShell based agent-less servers connect using PSRemoting over WSMAN. Could you please try to connect to your remote server using Enter-PSSession in PowerShell on your Otter server and try to run some commands to make a temp folder and write a file to it using the same credentials Otter users to connect to that server? It almost feels like there may be a permissions issue. The other issue seems like their could an issue with your OtterScript itself. Would you be able to share the OtterScript you are trying to run? Thanks, Dan