Help, Why won't my latest purchase from I-tunes sync to my I-pod nano?

Hey guys,

I downloaded a song by the Kongos and it will not sync to my I-pod. Is there a manual way for me to do this?

I seem to recall having this issue one other time and being walked through a solution, but I could be misremembering.

Anyway, any help?

Ok this is so obvious you’ve probably done it, but have you?

Updated to the latest version of the software.
Restarted your Ipod.

Yes, I did that. Oh well, thanks anyway. Maybe I can get Apple support.