The iPod Shuffle's Vanishing Music

I had noticed that the Shuffle reports way more "updating iPod" notices than it should, as well as the alarming message above, which occurs every time I plug in my player, including several times after it's been updated and nothing changes -- just clicking into the iTunes window causes it to worry. The podcasts flip their indicator from played to unplayed and back, and it locks up. I'm not sure if this is the source or not.
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Shuffleerror

I've been pretty proud of my 2nd-gen iPod Shuffle. It looks great, it weighs nothing and it clips on my shirt-tail. But it also ate a few dozen of my favorite songs from iTunes, and I can't find a culprit. Is it a new bug or an existing problem?

Your feedback will help us get to the bottom of it – read on for the full story.

Until I get a new computer, updating my Shuffle from scratch is a pretty slow process. My Powerbook G4 12" doesn't have USB-2, so the painfully slow data rates of USB-1.1 turn the procedure into a half-hour of fiddling.

As such, I've taken to a stripped-down update method that has done the trick nicely. I load up my newest podcasts at the very beginning of my playlist, fill about half of the rest of the space with a set of songs I always want in the mix after, then auto-fill to take up the rest. It works nicely, and I only ever replace about 3/5ths of the content, which is just enough to not drive me crazy. I listen to my podcasts, then switch to shuffle mode, and it gets me through the day with some variety and consistency.

Not ideal (still waiting on a new MacBook for that), but it does the trick. Except that one day, hitting autofill replaced everything on the Shuffle, including the songs that live on the player. Before you ask, yes, I unchecked "replace all items when autofilling". It was so sudden, in fact that I didn't notice until days later, when I couldn't find any of the music I had stored on the Shuffle – it was all random.

I had noticed that the Shuffle reports way more "updating iPod" notices than it should, as well as the alarming message above, which occurs every time I plug in my player, including several times after it's been updated and nothing changes – just clicking into the iTunes window causes it to worry. The podcasts flip their indicator from played to unplayed and back, and it locks up. I'm not sure if this is the source or not.

Anyway, I assumed I had just changed more music than I meant to and thought nothing of it, until Wednesday, when I noticed that my favorite song from Destroyer's "Your Blues" (the title track, as it happens), was just gone from my iTunes library. Similarly missing were the top 30 played songs in my entire library, all of which had been placed on my Shuffle.

I used Spotlight, but found no trace of the missing files. With a combination of my other iPod and audio transfer app Senuti, I was able to restore the lost songs with little difficulty. Senuti uses a little flag to mark which songs on the iPod it's examining exist in a given iTunes library, so it was no trouble at all to track them down. But if it weren't for the app's cleverness, this would have been pretty disastrous.

The songs are restored, and I'm handling the Shuffle with kid gloves. Has anyone had similar trouble? Has the problem been tracked to any one cause? Why oh why do podcasts make 2nd-gen Shuffles flip out?

Shout back in the comments thread, folks.