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

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!

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!

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!

I have the same problem. I have fixed and scanned my ipod classic countless times, restored, reset even tried assigning the ipod to a different computer and still I can only use about 5gb of my 160gb memory. I have paid to speak to the Apple Support who couldn't sort it out and didn't seem to have any real idea what the problem. When I took into the Apple store, their proposed solution was to sell me a new one!!!! I don't think so!

Hoping that by adding to these posts that I might add to the complaints about this problem and persuade Apple to actually help us all.

Anyway off to fix and scan, reset and restore AGAIN. If it hadn't been so expensive, I wouldn't be wasting so much valuable time on trying to sort it out.

I have tried every solution offered to fix this problem- dozens of resets and restores, drive clean ups, new usb cables, different ports, etc, etc. I'm just completely disgusted that someone from Apple can't come on this board and offer a real solution. I paid $400 not six months ago for my 160gb and now, through no fault of my own or my computer's, it's been rendered a piece of junk! On top of the money I spent on the device, I spend hundreds of $'s buying music at Apple and they do nothing to fix the problem!!! I'm so sick of hearing Steve Jobs being canonized- this is just another big company that enslaves its workers and treats it's customers like crap.

...Victoria, I'm curious if you were ever able to get yours working?

Thank you, but no, no photos. I have about 90 gigs of music in my library. I got the "160" (which doesnt actually hold 160) to better accomodate my collection. I only tried to restore in the first place because I was having skipping issues. I fixed all my tags, but about 10% of my songs would play for about twenty seconds, then skip to the next track. I guess I should have left bad enough alone.

I had this problem on my iPod touch. It was with my daughters computer account which is not an administator. I closed iTunes and re-openned 'As Administrator'. It worked. To do this, right click on the iTunes icon to select to run as administrator.

Hope it works!!

It depends on what version of what operating system your computer is on... Without that info you can try opening iTunes and clicking Edit > Edit Preferences and then click on the Device tab. Once in the device tab you'll see a window with a bunch of device backups listed, you gotta select and delete them.

If you have 2 iDevices with the same name iTunes won't let you dot that so you'll have to rename one (I'd suggest making the newer one a Jr. myself).

If you're on Windows 7 or Vista you can also go to C:\Users\<username>\AppData\Roaming\iTun… and delete the iPod and/or iPhone and/or iPad folders (while iTunes is not running) and then start all over too. It won't mess up your music or purchases at all, just gets rid of all of your device info.

You are brilliant. My first call to Apple did not help (though they kindly waived the 29.99 support fee); the second call, I couldn't make without paying for it. Your advice was golden. Thank you so much!