Per Max's astute observation in the comment below, the permission issue can be fixed simply by changing the 20 places that call remote_operations.py in evergreen.yml to use the Administrator user instead of $USER. We will likely refactor the code to set an evergreen expansion and merge remote_operations into resmoke as a new subcommand.
Powercycle has been failing on Windows due to an SSH permission issue. There is currently no easy way to investigate the problem due to an inability to access the ec2 instance running the powercycle test.
After chatting with Daniel Gottlieb, I'm postponing the work to investigate the permission issue.