I am running the latest version of iTunes on OS X 10.4.4 and also have a 4GB Nano upgraded to the 1.1 firmware, however, I have had the following problem for a few months and it seems to be getting worse: When playing songs on my Nano (and previously on my 3G iPod) the songs get cut-off. That is, as an example, 3 minutes into a 5 minute song it advances to the next song (note that the iPod shows the 5 minute song as being only 3 minutes... i.e. when playing it would shows 5 seconds elapsed and 2:55 remaining). When playing the same song on iTunes, it will at first show it being a 3 minute song but within 1 to 2 seconds update to showing it as a 5 minute song. After re-syncing my Nano, the Nano will play fine. However every day it seems there are another 2-3 songs with this problem. FWIW, all my songs are encoded at 192k AAC. Any ideas? I was thinking of re-importing all of my songs into iTunes (i.e. maybe the iTunes database is corrupted), but I have all my songs (4000+) rated and don't want to have to re-enter it.