Just got my 6th Disney GC at Walgreens using a Walgreens GC that I got from MyPoints.
I have gotten them at various stores.
If you ask, they will say "YOU CAN'T BUY A GC WITH A GC!"
Yesterday, for example, I got a Disney GC, and 4-5 other items (maybe $10-20 of other merch.), swiped my $50 Walgreens GC (I sometimes just say I am using 2 different cards) it takes off $50, then I swipe my CC for the balance,
The only time that I have had trouble is when I cut the amounts too close using coupons etc. I have messed up twice and couldn't get the card- but it was only that I tried to do too many GCs, or redeem too many rewards etc, and when they start to try to figure out why the transaction is not going through, they see the GC and assume that's the problem.
I work retail and if their registers allow the transaction, then I don't see a problem.
You cannot go in with a $50 Walgreens GC and Buy a other GC alone.
But it still works! I did it yesterday!