Mine turned out to be just because the Cypress driver didn't start automatically.
- Start ->Control Panel ->Administrative Tools -> Services
- Look for CyMiniProg3Service and start it (if it isn't already running)
- Restart the Driver Station application
If it's already started or the previous steps don't get it recognized by the Driver Station application, then you do need to remove the old Cypress software and reapply the Driver Station Update.
You might be able to either uninstall all the Cypress software yourself or run the Driver Station Update and choose the Remove option for what you can, then run the installer a second time to add it back in.
I'll run a few more tests to see what's necessary, but removing everything couldn't hurt.
I did note that without the Cypress board connected, I can use the virtual buttons in Compatibility mode, but not the buttons in Enhanced mode.