IPod Nano stops playing

My iPod Nano 5g stops playing a file (after 2 hours), but it plays Ok in iTunes to the end.   Latest software.  Manual synch. The file is long (29 hours of audio).   How can I get my iPod to play it through?   (Tried restore and recopy.)

I couldn't find any documentation regarding this, but I believe the 2 hour time limit is the maximum length your iPod can play of an audio file.  So you may need to break this one up if at all possible.  If not, I am afraid you are out of luck.
B-rock

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    Clean out the crud in the headset port. If you have tried #1 and it just won't insert all the way, it is likely that you have crud in your headset jack. Shine a light in there. The entire inside of the jack is white, so if it looks dark down at the bottom, there is probably crud down there. You can try blowing it out or using canned air. Just understand that shoving anything else in there to clean it out will be taking your warranty into your own hands! However, I have cleaned mine out using whatever was handy and small enough to fit in there and so far so good. Your results may vary!
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