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Adventures with Apple Pay

2014 October 20
by David Eads
My first Apple Pay transaction at Walgreen's went smoothly

My first Apple Pay transaction at Walgreen’s went smoothly

Like many payment geeks I downloaded the iOS 8.1 upgrade this afternoon then ran out to try Apple Pay with my 15 year old son.

The results were strikingly different than my adventures with Google Wallet and another NFC wallet on my Nexus 7 last year.

Just like last year, I decided to go buy candy (and a flu shot!) at Walgreens, Staples, and if desperate McDonald’s. Last year, readers didn’t work at all at Walgreen’s or Staples. Gruff employees had no idea what I was trying to do with my device and I was holding up the checkout.

This year with Apple Pay, my purchase at Walgreen’s was so smooth it was disorienting. It worked just like the demo video at the Apple launch. The only hiccup was that it was so smooth I forgot to change my default card to use my personal debit card. I ended up buying candy on my American Express Corporate card. (It’s a good thing I’m the CEO).

Staples, on the other hand, was an utter failure. I tapped my phone, tapped my phone, woke it up, tapped it again and got nothing. The irritated clerk said, “What kinda card you are you trying to use?”

I said, “Debit.”

He said, “That reader doesn’t work with debit, try credit.”

As the line started backing up, I switched the default card to my American Express. I tapped it again. Nothing. Again. Nothing.

I pulled my debit card from my wallet and swiped it to pay the old fashioned way.

As we were leaving, my son said, “Dad, it’s no wonder it didn’t work. Have you seen their computers? They’re like older than me.”

Based on my Walgreen’s experience, I think Apple Pay will be working smoothly for shoppers as retailers get their act together. When it becomes more than a novelty, which I think a few Apple ad campaigns will likely ensure, laggards like Staples will get their act together.




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  1. October 28, 2014

    As an update, I tried using Apple Pay at a Subway store in Underground Atlanta today. The well-worn Verifone POS equipment supported both barcode and NFC payments. The operator and his staff seemed familiar with barcode payments but hadn’t heard of Apple Pay. When I pulled out my phone, he was coaching me to turn the screen toward down toward the reader for the bar code reader.

    After three attempts, I swiped my card instead. At one point Apple Pay was engaged but either he canceled the transaction while I was trying to authenticate via Touch ID or my authentication failed too many times or there was a timeout. In short, there was a long line behind me by the time I was done.

    After my experience at Staples and Subway, I think retailers/franchises should put some effort into training customer facing staff. A few fliers in the breakroom would solve the problem.

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