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I got an American Express Gift Card for $100 over the holidays. It works like a credit card, but only has a $100 available balance, and you can’t get change from it or anything, so the only ways to spend it all without leaving any fragments behind (which I refuse to do on principle) are:

1. Buy something that will charge a credit card exactly $100, or
2. Order something from a place that will charge $100 to this card and the remainder of the balance to another card.

I wanted to spend it on an Amazon purchase tonight that was over $100, but Amazon has a little exception: You cannot charge an order to multiple credit cards if one of them is an American Express Gift Card.

Fine, I thought. I’ll use it to buy myself a $100 Amazon gift card, then apply the Amazon gift card balance to my own account, then place the order and pay the remainder on my real credit card.

Nope. There’s also an exception that you can’t buy Amazon gift card balances with American Express Gift Cards.

I was about to give up when my brain kicked in and figured it out.

1. I went to the last page of the checkout before purchase when it shows the total with tax and shipping. $435.81. Copied that number down, abandoned the checkout.
2. I purchased an Amazon gift card balance with my real credit card for $335.81. (Conveniently, this doesn’t replace or reset the shopping cart for the original order.)
3. I applied the Amazon gift card balance to my own account.
4. I went back to the checkout page for the original order. My gift card balance was applied, and the remaining balance to pay was exactly $100.00.
5. I paid for the order with the American Express gift card, using every cent.

Done.