Weird iPod Problem

When I sync my iPod each time it will not remember about 500 of them. This is annoying because each time I plug in my iPod it has to re sync those 500 songs and I have to wait on it. Even if the songs were there before it will delete them and re sync. I don't know what to do.

Thanks so much. All the other songs on my iPod work fine.

How do you have your sync setup? Is it setup to sync all songs, just selected playlists, or perhaps purely manual sync?

I have it set to sync just a certain playlist b/c my music library is larger than my iPod. It auto syncs.

is it the same 500 songs each time? i know thats kinda hard to gauge but it could be the songs that you've got. also check the playlist you're syncing and make sure everything is set up correctly.