Y..Y..Y, DOES NEW MUSIC APPEAR IN ITUNE BUT I CANT UPDATE IPOD...Y..Y..Y???

Hello, I've had limewire to download music for several months now and could drag music to itune then update my ipod, but recently the new songs I drag to itune from limewire are seen in my itune and can be played as well but when I try to update ipod the new songs don't appear. Nothing appears to be wrong with the ipod. I've tried resetting it, checking for upgrades both for the ipod and for the itune and nothing seems to work. Is itune now controling what can be updated to ipod. In other words, will the ipod only accept purchased music from itune?? Please help!! I'll appreciate it a lot...THANKS!

no i still use limewire to get songs and i can put them on to itunes. but what i do is i add the songs that i want to be put on to itunes into the playlist on limewire and save them to like my music folder and then i go on to itunes and click file, add file to libary and then it will be on the libary on itunes

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