"cannot be played on this iPod" - NOW WHAT?

I had an iPod mini that I sold last year and got a new iPod nano. I just noticed while transferring songs to it this message - that certain songs in my library can't be played in the nano! I paid for the songs. My question:
1. how do I identify what songs are being prevented from copying onto the nano?
2. How do I get permission to use all of my songs on my nano?
Important note: all of my songs were bought and paid for, so I don't understand why this is happening.

1. how do I identify what songs are being prevented
from copying onto the nano?
No easy way to tell, unfortunately. Look for songs that are not there which you expect them to be there. There are other ways as well. One way I used was to export my iPod's song list and my iTunes song list to text files, then imported them into a spreadsheet program for an easy visual side-by-side comparison. This let me find the problem songs very quickly.
2. How do I get permission to use all of my songs on
my nano?
It's not a matter of getting permission. For whatever reason, iTunes thinks that some of your songs cannot actually be played on the Nano. Maybe they're in the wrong format or something. If there are songs you purchased through the iTunes Music Store, make certain that you can actually play the songs in iTunes, this will ensure that iTunes can copy the correct keys to the Nano so it can play them too.

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