Songs not copying from iTunes to iPod

I am running iTunes for Windows, version 11.0.4. I have an 8GB iPod Nano generation 2, with software version 1.1.3 on it. I can play songs in my library through iTunes with no problem, and I can play any songs that are on my iPod with no problems when using headphones or plugged into an aux jack on my car stereo. Here are my issues:
When I attempt to transfer songs from iTunes to my iPod, the message "Copying 1 of #: <song name>" in the display (# being the number of sogs I'm trying to copy.) The problem is, nothing ever happens. No progress bar, no going onto song 2, nothing. It just sits there, and the eject button for the iPod shows the sync icon spinning. I cannot stop the transfer by clicking the X next to the message, it just continues on, doing nothing. To stop it, I need to click on the eject button, which does eject the iPod. When I look on the iPod, the one song it said was copying is there. I can play it and it works fine. When I plug the iPod back into my PC, I cannot see the songs on the iPod. They just don't show up. Turning the sidebar on, I see the iPod connected, but there is no "Music" option listed under it. In the new view, I can click on the iPod, select "On This iPod" and I see "Music" as a playlist, but there is nothing listed under it. When I click Autofill, all it does is sit there for a few minutes, saying that it is autofilling the iPod, but only one song shows up on the iPod.
To try and fix this issue, I have uninstalled and reinstalled iTunes, and also did a Restore iPod. Neither worked. I tried plugging my USB cable into a different port. The only thing I have not tried is a different USB cable, as I don't have one. Once I get one I can attempt that, but I doubt that's the issue, as iTunes has no problem seeing my iPod, just transfering songs to it.
Does anybody have any ideas why this may be happening? The worst part about this is since I did a restore, I now have NO songs on my iPod (except for the 2 that I did manage to copy onto it.) Thanks in advance for anybody that can help me out!

For some reason, hooking the iPod up to my wife's machine (which it worked fine on) seems to have done the trick. When I reattached it to my machine, it updates fine from iTunes.
Wish I had tried that first before restoring it.

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Some songs do not copy from iTunes to iPod

This is very frustrating. I have a 5th Generation 60gig iPod. There are about 20,300 songs in my library, none of them from the iTunes store. All legal, all owned by me and I have the CDs to prove it. When I update the iPod all but about 4 or 5 songs copy over. The frustrating thing is there's no way to find out which songs are not copying over to the iPod, so I can't tell if there's a problem with them or what. AppleCare tells me the only way to find out is to visually compare the list on the iPod with the list in iTunes. I have 20,000 songs here and allegedly one of the most powerful computers you can get and I have to compare two nearly identical lists visually?? Oh, by the way I'm running 10.4.6 and the latest version of iTunes and the latest iPod update. This never happened with my 4th Generation iPod. Any thoughts at all of what to do would certainly be appreciated.
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Are you basing the few that don't get sent to your ipod on the file count? Could there be duplicates? I've noticed that there are some of my movies that don't get sent over but I usually get a warning that they aren't in a compatable format.
There is an option in either file or edit (can't remember exactly where, I'm at work) but you can filter to show all the duplicates. I've noticed that when I drag files over to be copied to my ipod and there are duplicates, it only does one.
After you find the culprits, another thing would be to export the file to your desktop. Delete it from iTunes then reimport it making sure of the file format.
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I have been having a problem when syncing my iPod. At the end of the sync, a dialog box appears, saying 'some of the items in the iTunes library, including "song name", were not be copied to the iPod "iPod name" because they could not be found". In total there are 10 songs that I can not copy to my iPod, they were all purchases off Amazon Music, as I had a voucher for the site at that time. When I initially purchased the songs, they were copied to my iPod without a problem, it is only recently when syncing my iPod that this has occured. If anyone could explain to me how to fix this problem, I would be extremely grateful, thank you in advance!

Hi, zoed0775.
Thank you for using Apple Support Communities.
If an exclamation mark next to iTunes media in your library means that either the media is missing from the computer or iTunes is not directed to where the media is located. Here is an article that will help you locate the missing media. I have also included a list of icons in iTunes 11 as it will direct you to the best course of action.
iTunes: Finding lost media and downloads
http://support.apple.com/kb/TS1408
iTunes 11 for Windows: Symbols used in iTunes
http://support.apple.com/kb/PH12306
If the media that is missing has been purchased from the iTunes Store, you can delete the problematic media and download it again free by following the steps below.
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/HT2519
Cheers,
Jason H.

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I am having a very annoyingly difficult time. I am trying to add music to my iPod like I have been for years now. For some reason, iTunes is simply not letting me. I try to drag and drop a playlist onto my iPod, and the playlist is created on the iPod, but no music gets transferred! If I do the "sync" option, it gives me all kinds of problems with "can't find" the songs. When I show iTunes where the music is again, it still won't copy the songs over!
It seems the ONLY songs it will transfer over for me are ones that I had to convert to AAC because they were WMA format.
I have reset my iPod back to factory defaults, I have done everything I can think of. Nothing works, and it's driving me absolutely nuts!
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For some reason, hooking the iPod up to my wife's machine (which it worked fine on) seems to have done the trick. When I reattached it to my machine, it updates fine from iTunes.
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I have a new iPod, 5th generation 60 gig. I have about 20,000 tunes in my songlist. Four (4) of them will not load into the iPod from iTunes. I have AppleCare on my powerbook, so I called to see what could be done. I was told that I have to manually look through both lists to find which tunes aren't loading. We're talking about 20,000 songs. About 300 pages printed out, single-spaced. Hello? This is exactly the sort of thing computers are for. If there was a way to tell it to compare the lists I'd have my answer in less than a second. It might not be a big deal to the 200 or 300 song user, but I got the big iPod because I want to use it. Anyway, if anyone has any idea of a workaround, I'd surely appreciate it. Thanks a ton.
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Again, there's 20,000 tunes and over 4000 artists, most of them doing several tunes. There has to be an easier way than looking through lists. Everything is up to date. The OS, iTunes, the most recent iPod updater, everything. Every file is AAC. If it couldn't find a file it would, I think, say so. The basic issue is that there seems to be nothing built into iTunes to deal with the possibility of this kind of problem and I cannot for a minute believe that I'm the only person who has had something like this happen. And by the way, every file is a legal copy, owned by me.

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Songs not copying from iTunes to iPod

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