Currently with the PlayBook 1.0.1 AIR SDK the error reporting for signing and debug token issues can be far too generic. The biggest culprit of this is the BarSigner 500 unsigned error. The team is actively working on returning more specific error messages for all the various use cases. In the meantime here is a list of the reasons why this error would occur. Hopefully this will help you debug the issue faster when you see this error.
- There is no debug token on the device.
- The debug token on the device has expired.
- The debug token author does not match the author of the application being deployed.
- The debug token author id does not match the author id of the application being deployed.