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The Apple Pay Challenge: Hey, This Thing (Mostly) Works!

The credit-card authentication process can be a tad gnarly. But at the register, paying with an iPhone works as promised.

[Photo: courtesy of Apple]

When I resolved to leave my wallet at home and spend a week buying only those things I could pay for using my iPhone 6 and Apple's new Apple Pay service, I was prepared for the worst. I thought it might not work reliably—or at least turn out to be enough of a hassle to make me pine for my plastic.

Instead, the first couple of days have gone shockingly well, except for some issues getting cards verified for use with the service. I'm pretty confident I'm going to use Apple Pay quite a bit, even once this experiment ends.

Would you mind if I continued my report in the form of a conversation with myself?

What was the initial setup process like?

Apple Pay credit cards in iOS's Passbook app

For the first credit card I associated with Apple Pay—the one already tied to my iTunes account—it was a cinch. And the way you add additional cards, by pointing your phone's camera at the card and scanning in your name, number, and expiration date, is mighty cool.

But when I tried to jump through the security hoops required to use two additional cards (a Citi MasterCard and a Wells Fargo Visa), I couldn't. Citi said it was sending me a text message with a verification code, but it didn't come; Wells Fargo wanted me to use a special authorization app, which didn't work. (Each bank is in charge of approving its cards for Apple Pay, so the process varies.)

That was on Monday, when hordes of early adopters were getting themselves set up to use Apple Pay. On Tuesday, Citi told me that I was good to good to go. Wells Fargo, however, said I needed to call a toll-free number. I did, and got a recording saying I was verified—but Apple Pay still says that I'm not. (I'll try to troubleshoot further.)

Meanwhile, the debit card I tend to use for small purchases is from Ally, which doesn't seem to have announced any plans to support the service.

Where did you buy stuff with Apple Pay?

At Walgreens. (I've made a total of three stops at two different locations so far.) At CVS. At the Apple Store. And I've had lunch at Panera and McDonald's.

I only chickened out once, at a Subway. The sandwich chain is on Apple's official list of Apple Pay partners, but the joint was mobbed and the payment terminal didn't look obviously Apple Pay-friendly to me. Rather than asking them to make me a sandwich and then discovering at the last moment that I couldn't pay for it, I went to a nearby Panera.

Did the payment process go smoothly?

A contactless terminal at Panera, processing my Apple Pay purchase

It has. To use the phrase which Apple always aspires to—but doesn't always achieve—it just worked. Most of the cashiers I've dealt with were blasé about the whole thing, although the one at Panera called over a manager for consultation. (As far as I could tell, she was expecting the process to involve some special procedure; the manager told her to ring it up like any other order.)

One other thing: In its ideal form, the Apple Pay gesture involves lightly touching the Touch ID sensor on the iPhone's home button with your finger or thumb as you bring the phone into proximity with the terminal. That's pretty tricky to manage, especially if you're using one hand to hold something, as you well might be if you're out shopping. So I started by doing the job in two steps: phone-to-terminal, and then finger-to-Touch ID. That worked fine. But after a few encounters, I was doing it with one hand.

Is Apple Pay actually easier than paying with a credit card or cash?

Yes. At least for me. Certainly more so than Google Wallet was when I tried it a couple of years ago: That took too many steps to be a timesaver, and at that time, the whole concept of paying with anything other than a swipe of a credit card seemed to confuse more store employees.

Isn't a bummer only being able shop at the 34 chains which Apple has deals with?

Judging from the chatter on Twitter, this is a common misperception about Apple Pay. Actually, you can use it at any retail location with a contactless payment terminal which works properly. I did so at CVS—at an automated self-checkout, yet—even though the drugstore isn't on Apple's list. (MasterCard's MasterCard Nearby app is a good way to find retailers that should be Apple Pay-ready, no matter which credit cards you're using with Apple Pay.)

Apple, incidentally, singles out a few major chains as not being ready for Apple Pay, including 7-Eleven (where I was able to use Google Wallet in 2012) and Home Depot (where I wasn't).

How has this affected your shopping habits?

Well, for one thing, I'm entering stores through the exits, going directly to the checkout lines, and looking for contactless payment terminals. No point in shopping anywhere unless I'm confident I'll be able to pay when I'm done.

Was there anywhere you wanted to shop, but couldn't?

Oh, lots of places. I couldn't eat lunch at any of my usual haunts, and had to buy groceries at Walgreens rather than Trader Joe's or Safeway.

For now, at least, far more stores aren't ready for Apple Pay than are, even among big chains. But with an October 2015 deadline looming which will require many retailers to install new terminals, the odds are good that many more will be Apple Pay-ready before too long.

Have you cheated at all?

The closest I've come is going out to dinner at a nice restaurant, and letting my wife pay with her credit card. Nice restaurants, in general, are not set up for contactless payments, at least in the U.S.

Does Apple deserve all the credit for Apple Pay working well?

Definitely not. The company seems to have done a bang-up job of designing the iPhone hardware and software which makes Apple Pay work. And I'm impressed that it managed to wrangle so many banks into participating, even if the signup process on day one was bumpy.

But if Apple Pay is poised to succeed where past digital-payments forays such as Google Wallet never took off, it's in part because there are more contactless terminals out there, and the stores which have them understand them better. That's a revolution which was underway before anyone had heard of Apple Pay.

Any other thoughts?

It's worth noting that my experience has been anecdotal. Over on Twitter, most of the reaction I've seen to Apple Pay has been upbeat, but I have notice some folks reporting things I didn't run into, such as this:

One last question: Are you having fun?

Thanks for asking. I'm still at the point where it's a happy little novelty each time I use Apple Pay and it works. And the fact that it is working has left me a lot more optimistic that I may live to see the day when it really is practical to leave home without a wallet—or at least to carry one which is radically downsized from my current one, which looks like a tiny, poorly organized filing cabinet. So yes, I'm having a good time.

More news soon.