A revealing iPhone 11 headache

Sometimes, a mobile glitch is indicative of a much more pervasive issue. Such is the case with my recent iPhone 11 iTunes headache.

I’ll drill down into the details of the iTunes situation in a moment — along with a fix that Apple tech support swore didn’t exist — but the bigger problem here is the Apple experience. I’ve long been a fan of Apple’s products, because the company’s technology execution and GUI intuitiveness are exemplary. I’m not a fan of the experience delivered when upgrading — when I’m doing exactly what Apple wants to me to do. What should be a simple process is anything but.

Not that this is a novel observation. My friend Jason Perlow wrote about his bad Apple Store experience last month. Having read that piece, I figured I would avoid the friction points he flagged by setting up the carrier situation beforehand and by avoiding the in-store Wi-Fi. Alas, Apple had more surprises waiting for me.

This all started weeks ago when I placed an order for the iPhone 11 Pro Max. This was an upgrade from the prior line, so I thought the transition would be easy. (Now, now. It’s not nice to laugh at someone.) I decided I’d complete the carrier setup before the phone shipped, and then waited for delivery. When the arrival date came and went with no news, I called, and after suffering through multiple long holds, was told that there was some sort of a glitch and that instead of the phone being shipped to me, I’d have to pick it up at a store. Just as well, I thought, given that I had to do a trade-in anyway.

The rep asked what time that evening would I could pick up the new phone, so he could schedule an appointment. I said I couldn’t do it that night, but I would pick it up in two days. Sorry, he said, the system only allows us to book appointments on the same day. I couldn’t understand that. The Apple Store can be insanely busy. Wouldn’t it improve matters by allowing appointments to be scheduled days in advance? Another Cupertino mystery.

When I arrived at the store two days later, it was crowded, but a tablet-wielding…