If you have not already, restart your computer. Do this to reset the shuffle
Try doing a sync again. If the problem recurs... You are using the Sync button and syncing based on the settings on the shuffle's Music tab?
As a test, go to the shuffle's Summary tab, in iTunes. Check the checkbox for Enable disk use. Apply the change. This will make Windows see the iPod's "disk" continously, when it is connected. Try doing a sync again. If it works this way, it will provide a workaround, and a clue for why it did not work before.
I was able to make the Enable Disk use change without any problems. However, when I tried to Sync music again, I was given the error message: iTunes cannot copy "Song Title" to the iPod Shuffle because the file could not be found. I received this error message for every song. Windows also popped up an error message saying "Windows - Delayed Write Failed"
I went to the iTunes File menu and selected Library - Organize Library - Consolidate Files. Waited for it to copy all the files the the Media Library and tried to Sync again, but received the same error messages.
If you have not done so, you may want to restart your computer.
That message (about the song file not found) means iTunes cannot locate the song file where it expects to find it. Are you sure you can still play the song in iTunes (?), because you may get a yellow exclamation point next to the song, meaning the same thing; iTunes did not find the song file where iTunes expected to find it.
The consolidate command would not help if iTunes can't locate the files.
That might mean they were moved or deleted. If you do a Get Info (from right-click) on one of those songs, the Info window should tell you the expected location of the song file, on the Summary tab next to Where. Follow that path (using Windows) to see if the song file is there.
Yes, I have restarted my computer, as well as followed the link you provided and reset my iPod Shuffle.
All the songs play without problems or error messages in iTunes. I have no exclamation points next to the songs.
I used the Get Info on a few of the songs I'm trying to copy to the Shuffle, and I have found the file on my computer in that location.
I'm not sure what is causing this problem, but you may just want to do a Restore on the shuffle. Select the shuffle in the iTunes sidebar, under DEVICES. Over to the right, go the Summary tab. The Restore button is there. This will erase the shuffle, re-install its software, and set it to default settings.
When Restore completes, try syncing a small number of songs (maybe from one small playlist) to see if that works properly.
When trying to restore the Shuffle, I get an error message: Unknown error 1439
While researching this error, I came upon this page: http://http://support.apple.com/kb/TS1539
This is the error message that I am receiving every time I try to Sync. I completed Solution #1, but it has had no effect. As for Solution #2, I have to third party skins or themes or such things to delete.
I have purchased this shuffle to relplace a 2nd gen Nano that was recently stolen. I have had no problems syncing the nano on this computer.
If this is a recent purchase, you may want to contact Apple's tech support. If you have an Apple Store nearby, you can make a reservation at the Genius Bar. Or, within the first 90 days after purchase, you are entitled to "complimentary phone support"; click the Contact Us link at the bottom right corner of this page for contact info.
Either way, if the shuffle is defective, you can see about getting a replacement.