Not Copying From iTunes to iPod, No Error Message

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!
I would really appreciate if someone could help me find the way to fix this issue so I can keep using my iPod. Thanks!

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.
Powerbook G4, iMac G5 Mac OS X (10.4.6)

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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Tunes not copying from iTunes to iPod -- frustration

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.

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.

10 songs will not copy from iTunes to iPod.

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've been using my iPod for some time now, and this is a new problem for me. I have copied an audiobook (mp3) from the cd to iTunes. All the chapters show up there, but when I try to drag them to my iPod, only chapters 1 through 5 show up - the others don't copy. Any ideas? This has always worked before - I don't know what has changed!

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.
just a thought

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I've spent a TON of time copying artwork to some of the MP3's that aren't available in iTunes, and copied those songs over to my 30GB Video iPod. The thing is that the artwork isn't following the songs over. From my iPod I then have to manually find the cover on the internet, download it, and insert it into the individual albums, which takes a heckuva long time.
I've restored my iPod, but it still does the same thing.
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is there artwork for every song? like make sure they all have one, for EACH individual song, because mine didnt have all of them and it showed that it did, so i went through every song and made sure it had an artwork in the bottom left hand corner. it took a while, but im pretty sure thats the only way to do it. if this doesnt work, then i'm out of ideas...sorry

My iPhone 3G will not restore from iTunes. I receive error message 9. Any suggestions?

plz help

Did you ceck your security software setttings?
Error 9: This error occurs when the device unexpectedly drops off the USB bus and communication stops. This can occur if the device is manually disconnected during the restore process. This issue can be resolved by performing USB isolation troubleshooting, using a different USB dock-connector cable, trying another USB port, restoring on another computer, or by eliminating conflicts from third-party security software.

Error message while copying from iTunes to iPod

My daughter's iPod shuffle (1st gen) was not charging so I updated it to the lastest software (1.1.5). While doing so, iTunes required an upgrade as well (7.5). Both are updated. But it is still not charging. That's my first problem.
I decided to see if it was a problem with my computer. So I tried using my other daughter's iPod. It was charging and playing music. While I was at it, she wanted to add new songs. For some reason I had difficulties so I updated her iPod software to 1.1.5 as well.
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I now have an iPod that has no music on it. (Plus a second iPod that's not charging.) Both iPods are about 15 months old. They are shuffles (1st gen) and we have XP on our computer.
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Some formats that play in iTunes are not compatible with the 1st generation iPod shuffle, Aiff and Apple Lossless for instance. Apple Lossless is not supported on the 2nd generation shuffle: iPod shuffle: Compatible audio formats
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Quote: "If this option is selected, songs encoded in AIFF or Apple Lossless format are
converted to 128 kbps when transferred to iPod shuffle (the song files in iTunes aren’t
affected). Otherwise, iPod shuffle doesn’t play songs encoded in those formats"

Everytime I try to download a song purchase from itunes I get the error message. 'Unable to Download Song' could not be downloaded at this time. I cannot even sync with itunes on the PC.

Hi guys,
I need some everytime I try to download a song purchase from itunes I get the error message. 'Unable to Download Song' could not be downloaded at this time. I cannot even sync with itunes on the PC.
Kind regards
Ian

One correction, from the icloud I was not able to listed to the entire song. So when you purchased the song if it wasn't downloaded to your library, chances are you have lost your opportunity to listen to it.

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Hi,
I have downloaded app in my computer, since size was more than 500MB.
Now when i try to update or sync my app from itunes to iPod touch 5th generation, it not working.
It shows determining apps to sync and stops immediately.
I have disabled restrictions, resetted my ipod and tried to drag and drop.
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Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Reboot the computer

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I have the IPOD video 30gb, 5th generation, and have itunes 7.02..
I am able to download the podcast from itunes into my library, but am unable to download it onto my ipod. an error msg pops up:
"...was not copied to the IPOD because it cannot be played on this IPOD."
I've searched and searched for an answer to this, and it appears to be a somewhat common problem with the itunes upgradeto 7.02
does any one have a solution?!?
HELP! (i'm an ipod newbie-and this is driving me absolutely MAD!!)

OMG-i just figured it out!!
*first of all, i came across this in the itunes store help area-->
"Why won't some video podcasts play on my iPod?
Some video podcasts, while playable in iTunes, are encoded in formats that are not compatible with iPods. To convert those videos so that they are iPod-compatible, highlight the video in iTunes, right-click on the selection, and choose "Convert Selection for iPod". iTunes will automatically re-encode the video for playback on iPod. Go to the Movies section of your Library to find and play the converted episodes.
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I recently upgraded to ITunes 7.2 and although I have acquired new songs in ITunes when I connect my IPod it quickly says IPod update is complete but my new songs do not show up on the IPod.
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Gateway Windows XP

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.
just a thought

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Not Copying From iTunes to iPod, No Error Message

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