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OK, since Jerry got some assistance here, I'll give you a try.

I'm trying to synch my iPod with my iTunes library as I have added some music. But it won't synch! I've tried it two ways: pluging in the iPod and letting the automatic synch happen and I've opened the iTunes Library 1st and then plugged in the iPod. Both ways gives me a message that it has synched and I can eject it. Well, it wan't synched. So I rebooted the computer and tried both ways again. No luck. So I turned the computer off - loading updates beforehand - same thing - message but no music added.
Just the same tunes that were originally there.

What gives??????

How frustrating! I have had similar woes with mine lately but one time it erased what was there and added a total of -3- songs to the IPod. (So glad I checked it before I headed out for my run because one of them was Roberta Flack...I'd have been sleeping on a bench in Audubon Park.)

Make sure it isn't putting them in a separate folder on your IPod somewhere.
Also, make sure you have the boxes checked next to the new song...I have no idea if that matters but I just opened ITunes to look around and thought that might be the issue.

Good luck.

Well, it' a Nano so there aren't as many places to put things but both in music and shuffle it only shows the original songs that were on there...no new ones. I think I need to call a teenager...thanks!