Purchased songs can't be duplicated into iPod

I purchased some songs from iTMS and they are in my iTunes library and in a folder marked "Purchased" which automatically appeared when the first song was purchased. My problem is when I connect my iPod click wheel to my laptop, the purchased songs were not duplicated into my iPod unlike other songs that I copied from my CDs into my iTunes

It depends on your settings.
Did you set your iPod to automatically update all songs and playlist or update only selected playlists?
If the latter is the case, add the Purchased playlist to it.
You can add your purchases (they are in the Library) to any playlist you want.
Hope this helps.
M

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