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Apple Pay Gets Real: A Few Glitches, Many Successes, Lots Of Diet Coke

This article is more than 9 years old.

Apple pay went live Monday with support for most U.S. credit cards, from scores of retailers and with lots of fanfare. Still, the rollout wasn't without issues as users found cards that weren't yet supported and merchants who were unfamiliar with the service. A couple of days in to Apple's ambitious effort to replace your wallet with the iPhone, we've learned a lot about what works, what doesn't and what will (and might) be coming.

Citi gridlocked

My attempt to get started with Apple Pay began with a routine download of iOS 8.1 and then hit an immediate roadblock when I tried to add my Citibank AAdvantage card to Apple Pay. The Mastercard, which is supported, wouldn't sync up and eventually I found myself on hold with Citi. Thirty minutes later I was told to call back in 3 hours. Ugh. Fortunately, the Starwood American Express went it without a hitch as did most cards for most people. And, in fact, Citi appears to have fixed all its early issues as that card went in later, too. The Citi rep said they had "unexpected demand" for the service, which is surprising given how extensively they've been advertising it.

Anyway, armed with a working card, I went shopping. And shopping. I went where Apple Pay was supposed to work and places with NFC-equipped point-of-sale terminals where it should work -- even though the retailers might not be aware. Here's what I learned.

Shopping scorecard

CVS -- Not an official partner, but NFC-equipped nevertheless. I tried to buy a pack of Trident twice and my iPhone said "Done" on the screen. The sales clerk, however, said "it didn't go through." Given that the person in front of me felt spending 10 minutes complaining about their loyalty card with a line five people deep was OK, I wasn't going to delay anyone else. I paid cash and moved on. Score: 0 for 1

Walgreens -- Another drugstore, and an Apple Pay partner. Weirdly, after paying I had to hit OK on the screen of the payment terminal. Still, it certainly worked. Diet Coke #1. Score: 1 for 2

Apple -- This had to be a no brainer, right? Well mostly. I picked up an iPhone case I'm not sure I want. (A chance to test out returns via Apple Pay, perhaps.) Paying was fine, except Apple uses mobile terminals for payment and we both had to turn ours to face the other person's to make the connection. This was awkward and, well, let's just say this is one of those things that the guy before Tim Cook would have raged about. Score: 2 for 3

Subway -- I can't possibly reach the Verifone payment terminal. Fine when handing the card to the clerk, not fine if you need to use TouchID and pass your phone over it. Rather than have him move it from where it obviously normally sits, I give him my card and say nothing. This is a test, after all. (The Subway closer to my home would have worked as the device is near the customer, this one didn't). Score: 2 for 4

Whole Foods -- Totally routine. The clerk asks me, "Did it beep?" I dunno. There's a lot of beeping in a Whole Foods. Anyway, no NutraSweet products there, so no soda! Score: 3 for 5

CVS, Round 2 -- Third time proved to be the charm at CVS. And clearly I needed another Diet Coke after the long walk back from Whole Foods! One note is that a lot of the NFC readers are angled awkwardly, making them difficult to match up to the location of the NFC antenna on the iPhone. Maybe this will be easier over time, but it was finicky to have to angle the phone to kind of lay it against a tilted reader. Still... Score: 4 of 6

Target -- You can't pay in store with Apple Pay, but you can pay in app. It's a mess right now. You can only purchase one item at a time and the app was slow as can be. Still, it did work and it pointed out some interesting facts (1) Even if you aren't registered with Target you can buy something and Apple passes your e-mail to Target so they can send you order status. Presumably that address cannot be marketed to without consent, but time will tell. (I have my Target account on another e-mail, so I'll know.) (2) Target makes you enter a "pick up name" for in-store pickup. An inadvertent typo -- I promise -- meant they couldn't find me. Why doesn't it just use your name automatically and offer you a chance to change it if need be? Seems dumb. (3) Jason Del Rey of Re/code says the one-item-at-a-time glitch will be fixed within a month. Generously giving Target a win here. Score: 5 of 7

Staples -- Their PR folk sent me e-mail saying the app was live and working with Apple Pay. It crashed for me every time I tried to pay. Score 5 of 8

Chevron  -- The future, this isn't. No pay at pump. When paying inside, you had to pre-select an amount. This was like a 1985 experience using 2014 technology. Lousy for an official partner; still, I did pay with Apple Pay. No, I won't be doing it again. Score: 6 of 9 (that's two generous "pass" scores)

McDonalds -- Completely routine. "That was pretty cool," says the kid who sells me Diet Coke #3. Score: 7 of 10

Radio Shack -- "I don't think we can do that in the store," says the guy of Apple Pay. What he can't do, in fact, is sell me the Amazon gift card I'm trying to buy after 10 minutes. Why? Because -- and I can't make this up -- the card swiper on his register is not working. Finally, the two whiz kids there try a different register. I point out the NFC reader is live, based on the shining light on it, pay with Apple Pay, and start to leave. He continues some lecture about how it's not supposed to be working but I've long stopped caring. Score: 8 of 11

Rite Aid -- Another non-official retailer but with NFC. I figure drugstores are doing well, I'll press my luck. Sure enough, it holds. "High tech," says the guy behind the counter. I'm caffeined out and buy some caramels, instead. Score: 9 of 12

(UPDATE: In a move on can only describe as bizarre, RiteAid has apparently blocked both Apple Pay and Google Wallet. In order to do this, you have to specifically design your back end to look for transactions using those IDs and then halt then while still allowing ordinary NFC-equipped cards to pass through. In other words, you have to spend effort to inconvenience your customers. My local RiteAid is my drugstore of choice because it's nearby and on the way to/from many other errands. I'll be sure to let management know I'm going out of my way until they reverse this weird decision.) 

OpenTable -- Most of OpenTable's restaurants don't support "pay at the table" yet, so I pick the Menlo Grill Bistro & Bar my only choice in suburbia. Tasty food, but some weird issues with the technology. There's a $10 promo for using Apple Pay with Open Table; it won't accept it for me so makes me checkout again. Fine, but then three separate transactions show in my payment record (see image above). I'm still not sure how many times my card will be charged, but the aesthetics are bad at minimum. That said, OpenTable's payment product is great and once it's everywhere you'll wonder how you ever waited for a check. Score 10 of 13

Walgreens, Round 2 -- Move fast and fix things. In just a day, the need to confirm your Apple Pay payment on the Walgreens terminal is gone. The clerk says he doesn't know why or how, but it's done. Nice job Walgreens. Score: 11 of 14

Summary -- So in two days, Apple Pay worked nearly everywhere it was supposed to and mostly worked well. There are some ergonomic issues that are going to be hard to solve, I'd say. It's awkward pressing the TouchID while tilting the phone. It seems like Apple's NFC placement, while probably correct, isn't always real-world friendly. Mostly, though, that's something people will acclimate to and I'm sure waving the Apple Watch over a terminal will get popular quickly among Apple Pay fans. And, um, smartphone payment plus paper receipts is ridiculous. But fixing this is actually quite challenging with most point-of-sale systems, especially given Apple's mostly pro-consumer choices around privacy.

The larger issue, of course, is where NFC isn't, Apple Pay isn't. Some gas pumps may have support at the pump (readers, let us know), but probably not many right now. Lots of smaller stores keep their card readers out of reach and may not be aware that for a very small sum they can add NFC support to their existing system and be Apple Pay ready just like that. It will take some time. To that end, here's what's already under way.

What works, what doesn't, what might

Overseas support: Apparently, you can use Apple Pay internationally with U.S.-based cards. That's a surprise in that the technology wasn't supposed to be ready for that purpose yet. But a MacRumors post details success in Australia, the UAE and Canada. This only makes sense for U.S. citizens traveling abroad as others would pay a foreign-exchange fee every time for this convenience, which makes it less than worthwhile.

Amazon comingAmazon's Chase card is the only consumer card from that bank which isn't live with Apple Pay. The online retail giant tells GeekWire that will be fixed. It wouldn't say when or why it wasn't live on day one, but whatever bad blood exists between Apple and Amazon won't keep this from working for long.

Chase-ing Am-y: Speaking of which, Chase has published a handy guide showing precisely which cards work with Apple Pay. It's an explicit list and if your card (like my Chase Ink Business Plus) isn't on it, it won't work. That makes the list a bit different from the one....

Officially yours: ... Apple itself has up. The Apple Pay provider has everything broken down into categories, and what jumps out is that currently only Capital One and American Express are supporting small business credit cards. Apple also has a footnote warning that "some cards might not be supported" even in categories that otherwise are. (Cough, Amazon, cough.) Finally, corporate cards don't work either.

Will this change? Mostly yes, over time. In the meantime, 500 more banks are coming over the next 6 months -- or sooner. That will make the vast majority of personal cards available on Apple Pay soon.

Reasons not to swipeBank Innovation claims Apple will roll out loyalty and rewards on Apple Pay this year, instead of next year with Apple Pay 2.0 as many had assumed. Take this with a grain of salt, of course, but Apple seems to be set to bring advertising indirectly to Passbook, allowing you to send coupons and offers there for redemption. A rewards program where retailers could send you a specific promotion in store that was available if you pay with Apple Pay certainly seems to be in the offing, whether it comes this year or next.

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