You’re often better off not bothering with store credit cards and gift cards, but sometimes the rewards are too good to resist. Reader Shannon’s family had a clever plan to get extra discounts from Kohl’s and raise money for their kid’s school, but it didn’t quite go as anticipated. Two months of credit card payments vanished into thin air instead of being credited to their account because they used Apple Pay when paying off their bills in the store.

Here’s how the plan worked.

1. The family would shop at Kohl’s using a store credit card, since you get extra discounts of up to 30% for using the card. Since Shannon has the Kohl’s credit card saved in Apple Pay, he just has to tap his device on the card terminal instead of swiping his Kohl’s store credit card.
2. They would purchase Kohl’s gift cards through a fundraising program at their daughter’s school. Specifically, the school uses a program called Shop With Scrip. Families and other supporters order cards from a special site, and a percentage of each card goes to the fundraiser.
   At Kohl’s, these are a special gift card called Kohl’s Cares Cards, and the retailer specifically spells out that customers can use them to pay off their credit card accounts at a store.
3. Gift cards in hand, Shannon would go to a Kohl’s store and pay the credit card balance. This practice has become less common now that online bill payment exists, but in the olden days, paying off store cards was what you did when a deadline sneaked up on you or you were going to that store anyway.
4. Normally, to process an in-store credit card payment, a customer service staffer would swipe the credit card to identify which account was being paid. Instead, just like when he made the purchase, Shannon would tap his Apple device on the payment terminal.

The first time that Shannon did this, the payment appeared on his online account for a day, then it disappeared. Where did it go? Shannon couldn’t produce an electronic check facsimile made out to Kohl’s or proof of an electronic payment, because they paid with gift cards.

One manager figured out the situation, and was able to find and use a record of the payment being made. Everyone involved assumed that it was some strange system fluke, and Shannon used Apple Pay again when it was time to make another payment.

You probably already know what happened next. Once his payment disappeared for the second month in a row, customer service representatives and even store managers were unhelpful, with the managers simply telling him that they couldn’t waive the erroneous late payment fee or interest.

This second time, the manager couldn’t fix it, and Shannon spent six hours on the phone to Kohl’s customer service. Frustrated, he took his story to us, and we asked the media relations team at Kohl’s what was up. The elite customer service squad got right on it (we assume) and straightened out the payments mess, giving the family a $25 gift card for their trouble.

Sometimes money-saving schemes make things more complicated than they should be, and the mobile payment version of a credit card can’t do all that the plastic version can. Shannon could obviously buy things at Kohl’s with his store credit card through Apple Pay, but for some reason the payments weren’t registering when he used it to pay his store card bill.

Kohl’s did help Shannon and his family out, resolving the missing payment situation, but he says that they plan to cancel the store credit card. Even the occasional 30% discount isn’t worth the hassle.

We asked their media team whether this is something that’s been happening to other customers, or a known problem with their payments system, and they didn’t respond. Maybe Shannon is the only person who has ever tried to identify himself using Apple Pay while paying a bill in a store.

If you’ve experienced an issue like this at Kohl’s, or any other retailer, when trying to pay your bill, let us know.

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