Files that "remember playback position" are not updating during sync

I listen to long spoken word MP3 files that are not podcasts. I have the "remember playback position" option checked on these files. I will add it to my library, sync it to my 2nd gen iPod shuffle, then go play it. The shuffle will remember the playback position fine. When I plug it into the computer again, iTunes used to update the files on my computer with the new playback position from the shuffle. This is not the case anymore. The local files will stay at the spot where they were at the original sync (0:00 in most cases). The files on the shuffle will then go back to 0:00 as well. This is very annoying. Any ideas?
P.S. I'm using the newest Shuffle that was released along with the 4th gen Nano (mine is the 2GB blue).
I know this is supposed to work because I had a silver 1GB shuffle in 2007 that worked fine.
Message was edited by: ajstahl

ROFL I've named this thread "Shuffle Woes" in my favorites list. I seem to have fixed this strange and VERY elusive problem for now.
I discovered a duplicate music file that had the same metadata as another music file. The only difference between the two files was the name of the physical file on the hard disk AKA the file name. The metadata (tags) were exactly the same. Now that I've deleted one of the two files everything seems to magically work again. Don't ask me!
If the problem resurfaces again I'll be back. No more shuffle woes!

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