Yes, Just make sure that you buy him an Ipad for the carrier he currently has the plan on. Then you can disable thte current iPad and sign up for the new device. I would cancel that last day of your biuling cycle and restart there after. Not sure if you can split months? This all assumes month to month access with is what I have on ATT. Not sure if ther are other types of DATA plan but you shold check it out.