Following up on this: I decided to just go ahead and try booking multiple tickets via Pay with Miles. When booking, you select that you want to use Pay with Miles and choose a pre-determined amount of points to convert to cash (lowest you can do is 50k = $50). Unlike the gift cards, Pay with Miles will then be deducted from each and EVERY ticket. So, for example, if you're booking four tickets, the 50k/$50 will be taken from every ticket for a total of 200k/$200. You cannot choose which tickets on the reservation to apply the Pay with Miles (important to know since Pay with Miles is usually not as good of a deal as a straight-up points). When you're completing you're booking, it will show how much you will be paying in cash after applying the Pay with Miles for the total of all the tickets together. When it's charged to your Amex, it will show this total when the transaction is pending, but when the transaction posts it splits it up into individual transactions. So, for example, if you charged $100 to your Amex for four tickets, the pending transaction would say $100, but once it posted, it would break it up into four $25 transactions. All of the transactions say "Additional Collection" with the name of the person on the ticket. I booked the tickets 2 days ago. The transactions just posted this morning, but my meter hasn't moved yet.