Moved Files "Not Authorized"

Is there a step I am missing when copying new files to machines that are authorized to play my iTunes content?
Currently my iTunes libraries are located on external drives.
I have one for my desktop (G-Tech 2TB) and one for my MacBook Pro (iOmega Mini Max 2TB).
The problem I am having is with the "authorizations" on the files.
Even though both computers are authorized to play my iTunes content when I copy new files and go to play something new on my MacBook Pro the system invariably tells me that "this computer is not authorized to play this content". Now if I have an internet connection available this is an easy fix but if I don't (which is fairly often when I am operating off my laptop) I am screwed.
Is there a step I am missing in importing that will prevent this?

Hi kellmack,
Thanks for visiting Apple Support Communities.
I recommend the steps in this article if iTunes prompts you to authorize your PC to play some purchases after you've already authorized it:
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases
http://support.apple.com/kb/ts1389
Regards,
Jeremy

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PunkStar Studios wrote:
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