Probably this problem is caused by DRM --- Digital Rights Management which attempts to control use of digital media by preventing, access, copying or conversion by users to other formats.
Check your songs if with .m4p file extesion, if they are, then it is DRM to blame, the only way to solve this problem is using a DRM protected music converter to remove DRM
The referal tips bellow may help with it.
You cant. I deleted my library and redownloaded it a while back and i had bought a lot of songs and when i re-downloaded itunes i didnt have those purchased items or any others. your sunk.
you cant
well, last time i checked you could. its just a matter of clicking & dragging the song from the downloads section (once finished) and putting it into the music section of your "Library" in itunes
you cant. you have to have the music on your computer. and after that just sync it,
import them from the file button in itunes
Itunes will not import songs in Windows Media (.wma) format.
no you cant because the ipod was only made to read songs off itunes sorry
You cant illegally download songs from your iPod, it will allow you on computer, and then transfer to the iPod but other than buying from iTunes or Transferring from computer, you cant get music unfortunately.
AC/DC doesn't sell their music on iTunes.
you cant dowload bad music on itunes add him on facebook and get him to link you up
You cant transfer directly you must go on itunes on a compuer sync the music onto it and check the songs you want. Plug in your other ipod.
You cant just send them to it. you need a computer that has itunes and have both ipods on the same account and then plug in the old ipod to the computer and copy the songs to itunes then plug in your new ipod and copy your music to the ipod