I once was being checking out and the cashier (who I've gone through before) was having no problems ringing up my Disney GC's and then applying payment with a combination of Target GC's and my RedCard. Another cashier walked by and said "oh you can't buy gift cards with gift cards". I politely replied that Disney cards are actually merchandise cards and I've never had a problem. Even the cashier who was checking me out looked at her and said, "yeah just look it's ringing up fine and her Red Card discount is applying too". She just walked off and a minute later I saw her talking with a manager and pointing at where I was. Having just finished I just walked out without issue. Seems not everyone at Target is up on this. One thing I always do though is include at least two other non-GC items in my order. Milk, cereal or something else I need. If I plan to buy a lot of GC I coordinate it with my big shopping trip. Not sure it if matters but I think it helps from making people suspicious
because obviously I can use the Red Card/target gc for all the other items and the Disney GC just get rung up and paid for with the rest.
I will tell you something about Target "managers." Just because they are managers, does not make them pros.
First, I have been a cashier at Target for 5 years. In that time, I have outlasted many, many managers. Managers are hired straight out of college, with little to no Target experience. It's not like you imagine; that it was someone who worked up the ranks at Target. Management comes from the outside. So don't ever count on a "manager" to know the ins and outs.
2. when you ask to "speak to a manager" you get the "Leader on Duty." It isn't exactly the Manager of cashiers. It could be the manager of softlines, the manager of food, the manager of electronics. Yeah, they will "act" like they know what they are doing, but there are managers acting as "Leader on Duty" who hardly know how to run a cash register, much less know every vague, complicated coupon/discount issue. They will just BS their way through.
3. It doesn't matter if you buy extra groceries or whatever with your gift cards. The computer automatically adjusts the price.
4. Target Debit Cards are a little squirly about making a large transaction outside the norm. There's no rhyme or reason as far as the cashier can tell. I will tell you, I have owned a Target Credit card for 10 years and have never had this issue. As long as you stay in your credit limit that is. I know people are anti credit, but I would use a Target Credit card, and if you didn't want to wait for the bill, go to guest service before you leave the store to pay it off.
5. Front end managers, cashiers, Leader on Duty, may be "empowered" to give you the 5% discount if your Target card doesn't go through. This doesn't mean they *must* do it for you though. Just that they have the ability to choose. So remember to be nice. You catch more flies with honey. If you go in all huffy puffy rude, they may not choose to help you out. No one has to offer 5% when your red card doesn't work. And corporate WILL back them up, as not giving you the discount is not "wrong".
I think basically, go in, be nice and hope for the best. And if it doesn't work, go back later. Personally, I love the idea of getting the gift cards at target.com. You will get the 5% off, be able to use pharmacy rewards, get free shipping, know if your card went through, and no human hassle.
Hope that helped some!