IPOD - I-Tunes Purchased Music Problem

[nomad]

I bought my daughter a new NANO for xmas and used a gift card to go onto the I-Tunes store and redeem the card.

She purchased the songs, put them automatically into the I-Tunes library, and did an auto update to get them onto her NANO.

Trouble is, when she tries to play the song on her nano, the nano jumps over all purchased music and only plays music she has ripped from a cd and put on the NANO.

Anyone have any thoughts why she can't play songs she has purchased?

Thanks in advance...!