Error:some of the items in itunes can not be added...

We recently bought another ipod. We are using the same computer and the same accounts since we listen to the same music. My husband tried to add some music that I downloaded from the itunes store to his ipod and this is the message that he's getting "song of the items in the itunes library can not be added your ipod because you are not authorized to play them on this computer."
And it follows with a list of all the songs he can't add to his ipod, and they are all songs that we have downloaded with itunes.
Yes, we have played them on the computer itself to "authorize" them, I've read the FAQs, we just can not figure out how to add the songs to his ipod, and any help would be appreciated. Thanks!

I have the almost exact issue. Been using my iPod touch for a few years and recently have started to see that not all my video podcasts will update. I have tried tagging them as watched, unwatched, delete, download again, and nothing is working. I just want to watch my video podcasts. If you hear of or find a fix let me know, cause it is driving me nuts.
iPod Touch, Windows 7.

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Jellsworth wrote:
I've got over 100 of these when I look at the list.
for the avoidance of doubt, these files could not physically be on an external disk which isn't connected ? or could you have deleted the actual files from the iTunes music folder via explorer ?
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Error:some of the items in itunes can not be added...

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