Since I never know how often I will make it to Walgreens and I'd hate to waste a Register Reward (they expire in 2 weeks), I've figured out that I need to do at least 2 transactions during each trip. Anything that will get you a RR needs to be done in the first transaction, as long as you aren't doing more items than it requires to get 1 RR. I match with any coupons for those items and get the RRs at the end after paying.
If you are doing a second set of the same RR items do it in a separate transaction. Example- if you get $2 RR back for an item you only have to buy 1 of, do it in the first purchase and if you want another one, do a second transaction to get both RRs. They won't give you 2 RRs for buying both in the first transaction- you will only get one.
The last transaction is coupon-only items and non-coupon sale items. This way I can pay with all my RRs that I just got back (as long as there are an equal or above amount of items for the number of RRs used) and not have to worry about when they expire. Then just pay the remaining balance.
This is where you have to be a little prepared- make one list for RR items keep the coupons to match with it and then non-RR items and which coupons to match.
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