I have just added 2 new songs to my iTunes library that i want to put onto my iPod. Normally when i connect my iPod it will then just add the songs onto it automatically, but this time it won't and i have no idea why. I haven't changed any of my settings (in the preferences bit). It just comes up saying iPod Update Complete and then when i disconnect it and look for the songs i'm trying to add they still aren't there. What's going on? :confused:

Is the mark checked on the left next to the track name?

 

Latest version of iTunes and iPod software installed?

 

If yes, try to reset the iPod to default settings. (all data on the iPod will be erased, just sync again afterwards.

 

I hope I could help You with this.