iTunes Authentication

Back up his licenses and THEN reformat...................oh no too late :p

Seriously though has he tried logging into his itunes account and clicking the "authorise computer" option under the store menu?

Think its done on the basis of "being used on up to so many machines at a time" or something so he should just be able to re-authorise that machine .
 
Just check through the numerous iTunes options and as said above one of the options is "Authorise Machine" or similar and then everything will just start working.
It can be difficult to remember but you need to try and get into thje habit of deauthorising a machine first - because iTunes only allows 5 authorised devices per account.
However you can do a total reset once a year, so if you forget a couple of times and reach 5, simply revoke all machines, get your 5 count back and then reauthorise your main machine again.
 
When you try to play a protected file it should just ask you for your username and password - enter these and it works fine.

The only problem would be if either you've copied the files illegal to someone else, in which case it won't work which is the whole idea, or if you've reached your "5 computers limit". If the latter is the case, then up to once a year you can use a "deauthorise all computers" button which appears in your iTunes store account settings to reset the limit.
 
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