The talking about the possibility of a race condition between my manual execution and the Puppet service makes perfectly sense, I didn't realize that it existed before I read your reply above. As a matter of fact the powershell command described in my post is ran as a series of synchronous powershell commands before Windows restarts one last time to enter its normal state, as described briefly it is still in an installation automated state when the command is executed. Anyway one of the commands before the manual puppet run, that is the issue here, is the installation of the puppet agent package, it is installed via chocolatey and supplied with the host address to the master and the puppet ca. So my guess, bearing what you described above in mind, either the service or the explicit powershell command creates the keypair, that is almost immediately overwritten by the other resulting in the error message described. I can't investigate this using processexplorer as I am still in an automatic installation stage, but first thing tomorrow I will remove the manual run altogether as I think it is causing all the headache and is excessive as I presume that the Puppet service is already on top of things.... I'll post back with the results! Thanks Josh!