1st Generation Shuffle Issues with copying songs

See here: Some songs in iTunes won't copy to iPod

B-rock

That sounds odd... Between the times you connected it to your computer to fill it with music for your daughter, did the shuffle get connected to another computer?

If the shuffle had not been used in a while, you might try doing a Restore in iTunes. The Restore button is on the Settings screen, when you select the shuffle in the iTunes sidebar (under DEVICES). This will erase the iPod shuffle and put the latest version of software on it.

To fill the shuffle, you can try a different method that I find more convenient when I use my shuffle. First, create a new playlist in iTunes, and name it something that means it's your daughter's songs for the shuffle. Put your daughter's songs on that playlist.

Second, select the iPod shuffle in the iTunes sidebar (under DEVICES), and go to the Contents screen. At the bottom, it should say Autofill From with a drop-down selection box. In that box, select your daughter's playlist. Then, click the Autofill button, over on the right side at the bottom.

The iPod shuffle should automatically fill with songs from the selected playlist. If there are more songs on the playlist than can be loaded, a random selection from playlist will be used to make the iPod shuffle full. Going forward, you can just update the playlist with new songs and remove old songs, whether the shuffle is connected or not, and then click the Autofill button the next time it is connected.

That sounds strange. Did you end up doing a Restore? If you did, it won't be the causes I describe next, because the shuffle should have default settings.

At the botton of the shuffle's Contents screen, where you did the Autofill earlier, there is a Settings button. Click that button, and a window for Autofill Settings pops up. There's a slider bar there for Reserve space for disk use. It should be at zero (left end), but if it somehow got set toward the far right side, there would not be very much space left to store songs (maybe only enough space for ONE song). And you would not get an error message, because if the songs on the playlist exceed the space available, it's supposed to randomly load as many as possible.

Related to above, if you previously used the shuffle as a USB flash drive, it may have some data files on it. It would not be obvious in iTunes, but you should see any data files if you open the shuffle (as a disk) using Finder. If there are data files stored on the shuffle, they would be taking up space, leaving less space for iTunes to store songs on it. Again, if you did do a Restore, this would not be the cause, because the Restore would erase such data files.