I have no experience with upgrading to Windows 8. However, I have used PC Mover to migrate from XP to Windows 7. It did indeed move programs along with files. There is the option to choose which programs you want to migrate and which ones you want to abandon. There is the inevitable cleanup required to get everything functioning correctly. Some programs realize they have been moved and require new drivers or re-registering, etc., but all things considered, it was the least painful computer upgrade I have done over the years.