ITunes not copying all of my songs to iPod

I just recently got an iPod Nano 4th Gen new - and it worked great until recently. I just started getting this situation where when I go to copy over a group of songs from my library to the ipod it will copy maybe 5 or 6, and then stall out on one song and eventually have a write error. It froze my computer at one point and ended up needing to be re-formatted - which I thought would help. It didn't. I have no idea how to fix this problem - if it's something with my hard drive, something with my ipod, something with itunes - it's a tough call. Any ideas or help you have would be greatly appreciated!

Was it 'write delay' or 'delayed write'? Not sure if it makes a big difference in the wording, but a quick google points to it either being a hardware problem with USB ports and external drives, or system cache settings.
You mentioned it started recently...do you remember changing anthing about your PC's setup or taking any updates for any programs?

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Try this Discussion...
https://discussions.apple.com/message/19529357#19529357

ITunes not syncing selected playlists, choosing songs from all playlists

I have some smaller iPods that I use on random occasions. When I sync them, I choose the following options:
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iTunes not syncing selected playlists, choosing songs from all playlists
You have it selected to *sync selected playlists* and those playlists are not syncing to the iPod?
however this seems to be very counter-intuitive behavior for iTunes
It can be kind of confusing.
I suggest it's not a bug in that it is acting as it's supposed to.
The option (Fill free space) could be made clearer. Perhaps if they added "with songs at random from the entire library" or somehow added an option to select what the free space will be filled with.)
1) The fact that iTunes it is not obeying the selected options on the screen
Not supposed to do that.
If the playlists all fit and there is free space, what would iTunes use to fill the free space if it only used selected items?
2) iTunes is allowing users construct an unhonorable set of choices out of four options. If "Selected playlists, artists and genres" is not compatible with "Automatically fill free space," then that option should be grayed out.
It is compatible.
If there is free space after your selections are added, what should iTunes use to fill the free space? It shouldn't fill the free space with stuff already on the iPod.

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ITunes: Can't copy more than 6553 songs to ipod?

I've been having major problems with my music library on an ipod touch (5th gen, 64gb, iOS7, iTunes 11.1, mac mini).
The main problem is that I don't ever seem to be able to successfully copy all my music to the ipod. I'll do the copy and wait for it to finish, but when I later connect the ipod to my pc (sometimes several days later), some of the songs will show up in iTunes as gray, and they won't be visible from the iPod. I don't know if they were like that from the beginning (i.e. those songs failed to copy oririginally) or if they disappeared sometime between the copy and when I connected the iPod to the pc. If anyone has any idea why this problem is happening, I'd love to hear it.
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Hiya!
It depends on what kind of digital copy you have. This article goes ino details regarding the two types, and depending on the type you have, you may or may not need the DVD to redeem the code.
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ITunes not copying all of my songs to iPod

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