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Apple gets a lot of credit for putting effort into the user experience. Many attribute the success of the original Mac, iPods, the iTunes Music Store, iBooks, and their other products to ease of use. But building a brand based on user experience can be much harder than, say, a brand based on low prices (like Dell) or ubiquity (like Microsoft). Because it doesn't take too much to go from "it just works" to "it doesn't work," which has been my experience with iTunes 7. The worst problem: it freezes up whenever I don't have an internet connection. For a long time, I used WinAmp as my MP3 player. As a nerdy web developer, I'm stuck at my computer for inordinate amounts of time, so I tend to listen to a lot of music through my SoundBlaster. By long time, I mean 1997 through a few years ago. I didn't have much of my collection ripped, so a static list of the 100-or-so songs I did have converted was fine. After ripping the majority of my CD library, and getting my wife an iPod, I started using iTunes. WinAmp has media library features, but I just liked iTunes better. Fast forward to 2006, when iTunes version 7 appears. It added some cool features, like album covers. It also was pretty buggy. Apple has released a few fixes so far, but now with even the latest version - iTunes 7.0.2 on Windows 2000 - I run into issues whenever my Internet connection goes down, or I have VPN up and running, blocking all traffic. It will start up and play like normal, but then after a few songs, the audio cuts off. Sometimes the track looks like it is continuing to play, others the time stops ticking off as well. Skipping to the next track results in more silence. When I finally close iTunes, it doesn't really close - I have to go into the Task Manager and manually end the process. I've done some Googling to see if there was a solution, but so far no luck. I found a blog post by Don Loper talking about freezing, but disabling automatic checking for podcasts did not resolve my issue. I tried disabling Audioscrobbler, a great plugin that uploads what you've been listening to to last.fm, and anything else that looked like it might be trying to send or receive data. Still no dice. Now, this is obviously not a huge problem, but when I'm dialing in to work from home, it would be nice to be able to listen to music. I can always dig up WinAmp, but I don't want to bother importing or recreating playlists. My solution so far has been to listen to NPR on my headphones. The risk that Apple runs with each release of iTunes is that bugs, even if they are fairly uncommon, can put the breaks on the flow of the user experience like Fred Flinstone jamming his feet through the floor of his stony, Neanderthal car. Which is why all the hype (and the 6 month lead time) around the iPhone could still blow up in their faces. My advice: test, test, test, and do it with actual users. Oh, and anyone have any ideas to fix my freezes that I haven't tried yet?