First, I do not attempt to "break" each new implementation of a technology. It simply happens because the implementation has not been thought through. Companies rolling out new services on mobile phones need to think through the user experience. With payments this is even more important. If customers don't feel comfortable with a process they've tried, they will be hesitant to trust and return.
This experience described below is not mobile, but it involves NFC, and one can easily imagine a scenario involving cell phones which could go horribly wrong.
I drove myself to SFO (San Francisco airport) last week for a one-day business trip. I pulled up to the gate at the entrance of the parking garage to collect my ticket. Suddenly, my Speedpass "beeps." I think, "What?"
I roll down my window and there stands a parking garage attendant. She confirms that I want to use this prepaid SpeedPass to pay for my parking. (Please keep in mind that the cost of parking for one day will exceed the average balance that I carry on the card that I use to cross bridges in the Bay Area about once a month.) I tell her that I do NOT want to use SpeedPass to pay – I want to use my American Express card. (Ok, SpeedPass tied to my Amex card, but I don't want to use it this way.) She asks why as she undoes the recording of the time/date on my SpeedPass. I tell her that I am traveling for business and need a receipt. Duh? She scowls and punches a bunch of buttons on the machine so that it spits out a ticket for me.
About 24 hours later, I am leaving the garage. I pull up to the exit and once again my SpeedPass beeps. Sigh. I pull up to the unattended payment machine and try to insert my ticket. It doesn't want to accept my ticket because the SpeedPass has already been triggered. Sigh. I press the "Attendant button" and a man starts barking at me over the intercom. He claims to reset the machine so that I can insert my ticket. I insert the ticket, and the balance appears.
Now, I try to insert my Amex card. Machine doesn't want it because it still thinks I've paid. I finally get it in the machine, but the machine immediately spits it back out to me with such force that it flies out of the machine and under my car. Now, you have to imagine that I have pulled up close enough to the machine so that I can insert my parking ticket/credit card into the machine without leaning all the way out the window. This now means that I am too close to the machine to open my car door, get out, and retrieve my credit card from underneath my car.
Seriously, who thinks this stuff up? What was meant to be a convenient offering has now become completely INCONVENIENT. This is supposed to speed payment, but now there is a line of cars behind me. Besides, anyone who parks onsite at SFO knows there is seldom a line or wait of more than a minute or two. Have they checked the statistics on business vs. leisure travel? Business travelers need receipts – they need to know how much something costs. My company isn't reimbursing me for lump-sum amounts on a prepaid storage card of any kind.