itunes says 'the ipod cannot be synced A duplicate file name was specified?

I have the exact same problem! I have tried everything there is. Could the problem be caused by the latest iTunes update?

I had the same error report - duplicate file names, and the same issue - it would only sync a portion of my music after that. No playlists came over. After reading through the various fixes, some of which looked to be quite laborious, I decided to try the restore method. I assumed that this is like formatting a hard drive, which would hopefully erase any corrupted items. I did not have any music on the iPod that was not on my computer under iTunes (and backed up on an external hard drive), so I had nothing to lose. Restore worked - took about an hour to copy over 3000 songs back to the iPod. Note - I have the latest version of iTunes and iPod software.

"Because I don't have Windows 7 I had to go to My Computer, then right click on the ipod. Go to properties then tools then click "Check Now" on Error-checking. Checked both boxes and it scaned and fixed the problem. Thanks !!!!"

After two frustrating days I finally read this post and it solved my problem. Thanks!

That was a great solution! I got the error cleared! Thanks a ton!🙂

jerrodsdad wrote:

I had the same problem. This is how I resolved it. I have a Dell computer and Windows XP OS
1. I used a genuine Apple cable. I had tried one from Belkin and one I got from AT&T, but I could not get my IPod to sync properly.
2. Close ITunes.
3. Keep your IPod plugged in. Right Click on "My Computer".
4. Locate the image of your IPod and right click on same.
5. Go to properties.
6. Go to Tools
7. Click on "Check Now" on Error- Checking
8. There are a couple of boxes just below that you will need to check. It should start scanning.
9. Mine started scanning and then I received a message telling me the scan cannot be completed until I reboot my computer.
10. Keep your I Pod plugged in and reboot your computer.
11. Once the reboot comes up, the scanning of your I Pod will start. This will take a while depending on the size of your I Pod (I have an 8 GB, it took about an hour)and the number of errors on your I Pod's hard drive.
12. Once the scanning is done, disconnect your I POD
13. Open I-Tunes.
14. Hook up your I Pod. When your I Pod appears in ITunes, click on the I Pod icon and select Restore.
15. Go through the restore program and you should have your IPod working properly again.
16. Good luck.

Message was edited by: jerrodsdad.

I was having the exact same problems and operating on the same system as described above by the very helpful jerrodsdad.

Unfortunately, I can only make it to step 8. Once I click the two boxes and then hit the "Scan" button, nothing happens. The dialogue box simply disappears, and no scan takes place. I have tried this several times, clicking both options, clicking none of the options, and clicking each of the options individually.

The problem seemed to be that, when connected, my iPod was still "working." That is, the iPod display showed the "Connected: Eject before disconnecting" screen, and then the "Updating" screen with the cirucular arrows. My guess is/was that since my iPod was still trying to do stuff (rather than sitting there in "charging mode") that my computer was unable to do the error-checking scan.

In order to stop my iPod from trying to "work" I disabled it through the Properties => Tools options. Unfortunately, now my iPod doesn't even show up in the My Computer screen, nor is it found when I open up iTunes. Now I seem really out of luck!

Any ideas on how to fix would be welcome!

Was able to figure out how to get my iPod to start showing up again. But still unable to run the error-checking scan.

Same problem too but with a heap of other things. 🙂 I'm trying what Amdodge said now but seriously apple should do something, instead of making iphone 1000000 mabye focus on customer support? I mean, to call them I would have had to pay $49!