Notedown the timestamp when GPO fails and once you are logged in to machine, launch event viewer as local admin and check the GPO events under Applications and Services Logs/Microsoft/Windows/GroupPolicy. Once you start tracking each event since the time you started logon, you will definitely find something there to troubleshoot further.
Other than that you can also enable GPO logging on the machine (http://woshub.com/gpo-logging-using-gpsvc-log-in-windows-7/ ) and review that.
Thanks Shreyskar. I have enabled GPO logging in a test pool and working on recreating the issue so I can check out the logs.
We've had a similar issue where Machine GPOs were not loading, and this was due to the Daylight-saving-Times. Some machines did not have enough time to synchronize the time with the domain when booting up, which in return makes Machine group policies unable to load.
After every DST change, we have to open our master templates to synchronize the time, close the templates, take a new snapshot and recompose our pools.