music won't sync to my ipod classic 160gb

Error 69 refer to songs files being corrupted, so reconvert them or delete them.

http://support.apple.com/kb/HT1210

Did you Restore the iPod without any errors? if there are errors , you need to do a

chkdsk drive: /R /F

on the iPod drive:

Good luck!

Mine is doing the same thing and then an option pops up to fix the files and I do that and it still doesn't work.

Also, all the music has worked fine before why is it saying the error message now?

You indicate it has worked fine before. Think over everything. What has changed, either on your iPod or on your computer? Did you install any new drivers or USB devices? Update any programs? Add any patches? Expose the iPod to a different environment? Has nothing truely changed?

My ipod stays in the car, unless i bring it in to put new music on.. it's been cold, the only thing I can think of.

Leaving an iPod in a car is a bad idea, aside from the theft potential. The extremes of heat and cold that a car can face can damage the internal hard disk. Remember, an iPod classic is not like the newer devices: it is like your older desktop computer with a physically spinning hard disk, with reading heads floating microns above the disk. Heat and cold creates expansion and changes tolerances.

I'd suggest bringing the iPod inside, and leaving it inside for at least 24 hours to let it come to temperature equilibrium. Try that first.

Your response didn't address the other side of the equation: the iTunes you sync to. Have you updated iTunes recently or any other component? Install any drivers? Change the port where you plug in the iPod? Install any new security software, such as antivirus, that wasn't present when it was last able to synch?

I don't think anything is new. Anytime there is an update for itunes I download so I know I have at some point but not sure if has been since the last time I put new music on there. It's been inside for two days, I didn't try anything last night, but I'd really like to try and fix it tonight.

I restored it several times and each time it always says the music is corrupt when trying to sync.

Do a search on this forum for "corrupt music". I seem to recall there have been some others with a similar problem, and it relates to a corrupt MP3 header on music, and there seems to be a tool that helps with that. (rummages a bit) Try this. Note that I haven't used this tool, but it might help if the music is actually corrupt.

Did you try the tool I referenced above to see if the files were actually corrupt?

At this point, I'm stymied. I'd suggest walking it in to an Apple Genius bar. It is likely less frustrating than dealing with phone support or the computer systems.

Did anyone try to use Windows "chkdsk /f" to fix the iPod files corruptions, this simple fix does work or else you have to check the iPod HD health.

Do a iPod Disk diagnostic as posted by tt2, it may help in troubleshooting,

https://discussions.apple.com/thread/3110831?tstart=240

Sometimes you got just one bad cluster, which freezes the whole sync operations.

Of course I would always blame the freeze on iTunes 10.5, confilcts with Windows plug-in.