Supervision with Mac OSX Alternate Computer Connection

New Contributor III

Has anyone else had issues with being able to enable iPad Supervision with the option (checkbox underneath) to connect to other Mac OSX computers? It seems as though, even with this option checked, a message still appears that "this iPad is being supervised by another computer…" I have tried unchecking and checking both Supervision options, but nothing has changed. Even restoring the device(s) did not work. Any thoughts or suggestions? Any help would be greatly appreciated! Thanks.