Hello
firstly what hardware are you useing please send me a image of the rear of the pc
secondly makesure you turned on Allow engineer video options under system Admin> Security
lastly exit out of admin then shutdown jukebox then connect second screen and then restart jukebox
once jukebox has started go to the main menu and click on Engineer>Video Options
in there select the second screen
(please note you may have to config screens in windows itself)
Hope This Helps