I need some help. im getting error -69 when trying to sync my ipod. i dont kno what to do. ive tried googling as much info as i can on this but i cant seem to find a answer to get me off to a good starting point. i back all my music up on a hard drive.

i need some help. im getting error -69 when trying to sync my ipod. i dont kno what to do. ive tried googling as much info as i can on this subject but i cant seem to find a answer to get me off to a good starting point. i back all my music up on a external hard drive.

If the file was not originally from iTunes, you'll need to redownload it from it's original source or rerip it from the CD.  Files can sometimes go bad and become corrupted.  As to how or why that happens, there are a number of ways.
What format are the problematic tracks in? Have you tried converting them to another format in iTunes?
iTunes: How to convert a song to a different file format
B-rock

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