I did try the first option already to no success. I don't want to do the manual stuff until it's a last resort. If more machines have this issue it will become a nightmare to get done, I'm managing this to an entire school district and doing it remotely is extremely efficient. I did notice something odd in the license administrator section though. It looks like the license was sent twice to the same machine and even has the check marks that it's activated, but it looks different from the other machines. The machine itself however says that the machine is still not activated though.