Q: iPod Classic 7th Gen 160GB won't sync

I am having the same problem.   Did you resolve this problem.

The last time I tried it said the data was corrupted and couldn't sync but it syncs with my iPod just fine and it's the exact same style.

If you are doing the same sync, and it works fine on your iPod, the iTunes files on the computer are probably OK.  I assume you are using the same USB docking cable (so it's not a bad cable causing this problem), and the same port on the computer.

If your friend's iPod is the type that uses a hard drive for storage (a "classic" iPod), the hard drive may be faulty.  This is more likely, if the errors always start occurring at about the same point during syncing.  When you do a Restore, only a small amount of data is written to the iPod's drive, so no error occurs.  That portion of the drive is OK, and the rest of the drive is empty.  But when you start syncing iTunes song data, at some point, the syncing reaches a portion of the drive that is bad, and iTunes is not able to continue.  Since your friend's iTunes library is not as large as your library, when he syncs his library to his iPod, it may not get to the point on the drive where the errors occur.

That's one possibility...

It may help to know the iPod model.  You said "it's the exact same style," so they are the same model with same storage capacity, correct?  You can check this document, of you're not sure about the iPod model.

Identifying iPod models

If the cause is a faulty hard drive, there is no software-based fix.  Do you use a Mac or Windows PC?  You can set the iPod to Enable disk use (on the iPod's Summary settings screen in iTunes), and Apply.  This keeps the iPod's disk mounted by the system.  Then, depending on Mac or Windows, use the system command for reformatting (erasing) the iPod's hard drive.  I can provide more details if needed, depending on Mac or Windows.

If the computer succeeds in reformatting, run Tunes and do a Restore.  The Restore re-installs the iPod's onboard software.  Then, try doing a sync again.

I'm a Mac user, so I don't know the exact step-by-step directions, but if you do an Internet search, there seem to be many How-To's for reformatting a hard drive using the Windows tools.  But here are some specifics.

If there is a step to initialize the drive, select MBR (Master Boot Record).  Since this iPod was already being used under Windows (not a Mac), it is probably already initialized.

If there is a step to partition the drive, you want to create one partition that takes up all the space on the drive.

For the disk format, select FAT32 (or something "FAT").  Do not select NTFS.  Select to do a full format, if there is a choice for a quick format.

When the reformatting is done, run iTunes and do a Restore.  Then, see if syncing works any better.

I am having the same issue. I have a 160 g classic that was formatted and used on a Mac. I have a Windows 8 computer now. So I knew it wouldn't work on it so I installed latest version of Itunes and connected the Ipod and restored and formatted for Windows. No problem. I tried to sync and the Ipod is shown in Itunes and says 148 gb free. I check either manually manage or uncheck it doesn't make a difference. The Ipod within 3 seconds says the Ipod sync is complete and OK to disconnect. Of course, there is no music on my Ipod.

I'm having this same issue. My ipod is formatted for PC and I have a PC. I had restored my ipod because it was lagging and freezing. Once it was restored I tried to sync all the previous files that were on the ipod and within less than a second the ipod "sync is complete" and says "eject before disconnecting" and no music files were uploaded to the ipod. ipod software is 2.0.4 and I'm using version 12.0.1 of itunes.

Anyone know how to fix this issue?

Has anyone come up with a solution to this?

I'm trying to Sync ~8000 songs either automatically or manually, and even in small (40 song) batches, I always get an error code (-50), (-53), or (-69) on a random song and the sync freezes.

I've reformatted and restored on both a Mac and a PC.

Uninstalled, reinstalled iTunes and other Apple software.

I've consolidated my library, and everything plays fine within iTunes (i.e. no missing file locations).

Tried pretty much every other 'solution' found on forums, to no avail.

Windows 8 / iTunes 12.3.2.35 / iPod Classic 160GB (late 2009) v. 2.0.4

The likely cause is a faulty hard drive in the iPod.  There may be a portion of the disk media that is damaged.  Doing a reformat or Restore in iTunes does not use that portion, so it works. But when iTunes tries to write song data to that portion, the sync process "freezes."