-69?

In the course of your troubleshooting to date, have you worked through the following document?

iTunes displays a -69 error when syncing iPod

Yes and no matter how many times I sync and delete the problematic files, it always finds new ones it has an issue with and wont let me progress..

Okay. On occasion, that can indicate a hard drive going bad under your content files. So, just in case, try running a disk check (chkdsk) over the drive containing your content files.

XP instructions in the following document: How to perform disk error checking in Windows XP

Vista instructions in the following document: Check your hard disk for errors

Windows 7 instructions in the following document: How to use CHKDSK (Check Disk)

Select both Automatically fix file system errors and Scan for and attempt recovery of bad sectors, or use chkdsk /r (depending on which way you decide to go about doing this). You'll almost certainly have to schedule the chkdsk to run on startup. The scan should take quite a while ... if it quits after a few minutes or seconds, something's interfering with the scan.

Does the chkdsk find/repair any damage?

i got a brand new computer last year and could not sync my old ipod to it. i got the same -69 message. i gave up when i couldn't find anything on the web that would help solve the problem.

i just retried again, but nothing new. it'll stop on a different song with the same -69 message. did the chkdsk recommended by b noir solve your problem?

doing the chkdsk didn't do anything. i still get -69 error on different songs when trying to sync the ipod.