This matches what I've seen with iOS @jared_f. As long as you have the device entered in DEP and have settings assigned through Dashboard, DEP enrollment will properly happen even after you restore from a backup that was not previously DEP/supervised. I will note that this does NOT work for Mac's. If you have a Mac that's enrolled in DEP and then you restore an image of that Mac to another Mac that has DEP settings assigned, the second Mac will not be enrolled in DEP.
... View more