Yes you can. I do it all the time, not with gas though.
Every branded gift card in a preset dollar amount will count as a grocery purchase. The Visa and Mastercard gift cards, which you select the the dollar amount, charge an activation fee, diminishing, if not negating the reward totally. If a grocery store sells it, it will count as a grocery purchase. If a restaurant sells it, it will count as a restaurant purchase. Does Cracker Barrel have two seperate registers? One in the 'store' and the other to pay for your food? If so, this may be the exception. The multiple register counterpoint; prescriptions filled at the grocery store pharmacy. The last time I did it, it counted as grocery.
I just added $100 (an amount of my choosing) to my Subway card, at Subway, with my Discover More card and I will get $5 in rewards for it. I added $100 (again, of my choosing) to my Sears gift card, at Sears, and I did get $5 in rewards for it.
During Q2, with Freedom x3, I will be buying many gift cards at my grocery store... ebay and amazon among others and many for the grocery store itself, they can also be used at their pumps.
Now for the nit-pickers around here...
Pay at the pump is coded differently, if your grocery store sells gas. All the above is subject to your merchant being coded correctly. Kroger grocery showing up as gas, both inside and at the pump, comes to mind. Verify your grocery store(s) show on your statement as such. Unfortunately, Chase will show these as 'other', it's ok.
One last point. If I'm buying milk, bread and a Bass Pro Shops gift card at the same time there will be only one transation code (one total receipt and one for each gift card you have purchased verifying activation), all completed under one merchant code. Grocery.


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