New iTunes lies about iPod contents

New version of iTunes, new weirdness. I updated iTunes to 7.1 at the end of last week and now I’m having podcast syncing/copying problems.

My iPod nano is usually synced to my work computer, an iMac. On Friday, when I connected the two, the nano was supposed to get a copy of the latest episode of In Our Time, a BBC Radio 4 show. According to iTunes, the show didn’t sync. I tried unchecking and rechecking that podcast for syncing, unsubscribing and resubscribing to it, dragging it to the desktop and reimporting it into iTunes so I could add it to another synced playlist; nothing worked. It never showed up in the list of stuff on the nano. But when I disconnected the nano and looked for the podcast on it, there it was, right where it was supposed to be. And I could listen to it. I then hooked the nano back up to the iMac to look at its contents again in iTunes, and the episode was still nowhere to be found. [I’m now pretty sure it was the dragging to the Desktop and reimporting that put the episode on the iPod. See the updated update below.]

This evening, I wanted to add the latest episode of Harry Shearer’s le Show so I could listen to it as I bike into work tomorrow. (Spring has come to Chicagoland, and I want to take advantage before it goes away again.) I got the podcast into iTunes on my iBook and connected the nano. I switched the nano’s setting from automatic syncing to manual management and dragged the new le Show episode to it. As you’ve probably guessed, the episode did not appear in the iTunes inventory for the nano, but did appear in the nano’s own list when disconnected. But not as a podcast, just as a regular music item.

I’ll Google around a bit to see if others are having this problem. If not, I’ll file a bug report with Apple. I hope it’s well known and the fix comes soon. It’s no fun not being able to rely on iTunes to give you an honest accounting of what’s on your iPod.

Update I forgot to mention that the In Our Time episode on my nano that didn’t show up in iTunes on on my iMac did appear in the iTunes on my iBook. I don’t know if that’s significant, but I do know it’s weird.

Updated update I’m still not sure of the root cause, but I found that the podcast episodes that refused to sync (there was also a recalcitrant Coverville episode that I didn’t learn about until this morning) had something in common: their Options tab in the iTunes Get Info window was grayed out. I have no idea why this was the case, but it was unique to the troublesome episodes.

A temporary solution was to drag a copy of those episodes from iTunes to the Desktop, delete the originals in iTunes, then drag the copies back into iTunes from the Desktop. The Options tab for the recopied episodes was black and they synced just fine.

The permanent (I hope) solution was to unsubscribe from the podcasts, delete the problem episodes, then resubscribe. The new copies of the just-deleted episodes that were downloads didn’t have the grayed Options tab and they synced.