this is a windows issue, go to your control panel, administrative tools, services, and make the terminal Services service start automatically, the newer wacom drivers depend on this service for support of user defined settings... problem is by default the service is set to manual. i had all kinds of problems with it and installing my tablet drivers over and over again until i found this issue posted on the wacom forums.
This was happening to me all the time at work until I realised that the message which pops up is lying I just found that restarting the computer fixes the problem, but arshlevon's fix is far superior Thanks, this'll save me a lot of time!
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Alex