After reading a lot on the blog Frequent Miler, I decided to do my own experiment with double dipping the Ultimate Rewards shopping portal with the highest paying merchant magazines.com at 35 points/dollar. 1. I went through the portal to magazines.com and bought a gift certificate for $28. (According to the terms and conditions, gift cards are allowed) 2. I went through the portal a second time and placed an order for magazines for total of $27.49 and used the gift card to pay The following is what posted: Order #1: Transaction amount $28 - Points 980 Order #2: Transaction amount $13.73 - Points 480 I found it odd that the amount posted for the second order was 50% of the amount that i actually spent ($27.49) Regardless, 1460 Ultimate rewards points for spending $28 at magazines.com That's 52 points / dollar.... awesome!