During a XenDesktop 4 to 5.6 migration I had to deploy WinRM on Windows XP SP3 virtual machines. I had a Desktop Group of 60 Machines for developers with IIS installed on it. WinRM installation went fine but the configuration wasn't possible, I always got an error when the service was trying to start : The WinRM service is unable to start because of a failure during initialization. Additional Data The error code is 1300. After trying to understand what was wrong I found in the Local Security Settings / Local Policies / User Rights Assignment / Generate security audits, only LOCAL SERVICE was authorize, so I just try to add NETWORK SERVICE account as well. Then and at last WinRM service was able to start normally. Now everything is working like a charm with Desktop Director.