Originally Posted by Points Scrounger
Yes, each separate transaction of $15+ should get a bonus. However, others have reported here that multiple charges linked to the same airline from the same restaurant on the same day do not (usually) post automatically. Don't be surprised if you end up having to send those receipts to Rewards Network for credit.
Vary each transaction that is linked to the same airline from the same restaurant on the same day by a penny, and you'll be fine 99% of the time. When the airline sees the multiple transactions identical in amount and in the same day/restaurant, it appears as if Rewards Network made a mistake by posting multiple identical transactions.
I purchased 4X $20 gift cards at the same place (each transaction just minutes apart), but charged them at $20, $19.99, $19.98, $19.97 (the difference I paid cash in pennies). They all posted with no problems.