Hi Jubal,
Sentinel UltraPro is a very old product.
Supporting it on newer operating systems may also depend on the version of UltraPro components used in the application.
We do not officially support any USB to Parallel converters. However, you can try the same and check if it works.
Regarding upgrading the key to USB type, you would have to check with the application vendor. They should be able to provide you the new USB key.
In either case, please use the latest drivers (includes USB and parallel drivers):
Regards,
Ashish
Ashish