Hi Moritz,
We’re running into the same Problem when trying to register the Windows Agent using Ansible (winrm/ PowerShell).
It looks like it is currently not possible to register the agents automatically, since the certificate store is remote not available.
Since you build PS manually, maybe you can build a workaround using this information: Adding a Certificate to a Store Using PowerShell -- Microsoft Certified Professional Magazine Online?
In total, a fix in the Agent would be nice to simplify the registration workflow.
