It's definitely a case of YMMV. Based on my experience with coupons and sales, I know that different Walgreen's stores within a few miles of each other will have different rules based on how lenient their managers are. I have yet to find a Walgreen's in my area that will allow you to purchase a gift card using a Walgreen's gift card. I'm just not that lucky. So, I use my mypoints rewards for other things.
I just had a discussion with a Walgreen's chat person, and she confirmed that you CAN purchase Disney gift cards with Walgreen's gift cards (in store only, not online). Her name was Lisa (for reference if needed).
I've done it at least 5 or 6 times! Only once did the clerk need to confirm with a manager that it was allowed and how to do it. I have usually had other things to purchase at the same time and put the balance of my total on my debit card. I don't know if that makes any difference, but if it works, I will keep doing it!
Just a couple days ago, I used two $10 walgreens gift cards to buy a $20 PlayStation Network card. I had gotten the gift cards on black friday free with buying itunes cards. I did not ask and it was no problem at all.
I've done it successfully several times. I usually throw in a small item like a card or pack of gum so the total is slightly more than the Disney gift card.
Waiting for another my points walgreens redemption to arrive so I can go do it again.
I just did it Thursday afternoon when I also used the Lindt coupons. I just have the card rang up seperately and then slide the gift card same as you do credit cards. I have not had a single problem. Just make sure that if the gift card is fr $50 you only get the Disney one for $50. I have not even given the cashier the card.
It works at all 3 of our Walgreens. I would try it without even telling the cashier you are using a gift card.