The problem is that changing the Comment field in iTunes does not usually change the Date Modified field. Without this, iTunes doesn't know that it is supposed to move the updates to your iPod during an autosync.
Since you probably have already made a large number of Comments changes, the easiest (read: least effort on your part) change is to Restore your iPod to factory settings, and reload the entire library on the next sync.
In the future, as a workaround, when you change the Comments field, you should also make a change to a field that you don't use (such as Composer or BPM).
Also, submit a request to Apple to fix this.
by thenightfly42 on Nov 12 | 7:25 am
Thank you, thenightfly42!
You got it right on the money. I had several CDs where each track had "DesertIsland" in the comments field and a Smart Playlist called "Desert Island Discs" set to look for that phrase. Testing your suggestion, I added album artwork to one of the discs and, on the next sync, it showed up in the previously empty playlist.
Next step...restoring to factory settings. And you can bet I'll be letting Apple know about this.
Thanks again. I was totally stumped on this.
by Michael on Nov 12 | 10:59 am
Wow, I didn't know that.
You could also do something like control-clicking the songs and choosing convert id3 tags.
The problem is that changing the Comment field in iTunes does not usually change the Date Modified field. Without this, iTunes doesn't know that it is supposed to move the updates to your iPod during an autosync.
Since you probably have already made a large number of Comments changes, the easiest (read: least effort on your part) change is to Restore your iPod to factory settings, and reload the entire library on the next sync.
In the future, as a workaround, when you change the Comments field, you should also make a change to a field that you don't use (such as Composer or BPM).
Also, submit a request to Apple to fix this.