My First Truly Crappy Apple Experience

I’m coming up on 2 years into my MacBook/OSX life, and while I’m not quite a drooling fanboy, I am most certainly drinking some of the Apple flavored Kool-Aid.  Why? Because everything just works, almost all of the time.  Seriously.  I do have the occasional frozen application, and have been forced to reboot against my will periodically, but it’s a rarety.  And I still miss Windows keyboard shortcuts, iMovie is horrendously bad next to Windows Movie Maker, and Mail/Calendar could use some help too.  But for the most part, I heart my MacBook and recommend them to everyone who asks.

Yesterday, however, I had one of those “What The What?” moments with an Apple application.  One of those “I’ll bet Steve never saw this user flow” before thoughts.  Here’s the rough sequence of events…

1. Inside iTunes, I went to the Store.  Easy.
2. Looked for TV Shows.  Easy.
3. Found Kids category. Easy.
4. Found Thomas the Train.  Easy.
5. Bought an episode.  Easy.
   While my wife and I *rarely* entertain our son with TV programming, we had a long day in front of us and wanted to have a lot of backup ready, just in case.  Thomas the Train, muted, was our selection, mainly because we didn’t have the ability to buy old Montreal Canadiens hockey games.  Which, of course, are perfect for children of all ages (as long as you remain in the years prior to 1994).
6. Paid for the episode. Easy.
7. Watched the episode download to my hard drive. Easy.
8. Closed the lid. Really easy.

   several hours later (yup, after about 7 hours the moment struck – we were exhausted, kids missed nap time and we were just out of steam to keep anything interesting)…

9. Opened the lid. Easiest step so far.
10. In iTunes, clicked Library, then TV Shows. Easy.
11. Found Thomas the Train, double-clicked on the episode. Uh oh.

Here’s the first dialog I saw:

I was being asked to authorize this computer.  Now, as an interesting point, I’d never, ever, purchased anything from the iTunes store before. Here’s the problem – I was offline by now.  And I was pretty sure what would happen next, but I clicked through anyway.  As a result, here’s the next screen I saw:

And huge whopping frustrating FAIL.

So my note to team iTunes: when a user makes their first purchase from your store, you should probably get the authorization thingamajigger to happen at the same time.  If not, warn them, in a big honking font, media will not play until you authorize your computer (and you will need an Internet connection for this). Don’t worry, I’m still BFFs with OS X and everything, but this is an easy thing to fix. And even if it only happens to a tiny fraction of a percent of your customers, it’s too easy not to do it better.