Cant Play Some Songs in My iMac Downloaded From the Cloud

Hello,
Can anyone give a tip to solve this out?
I've signed up for iMatch in order to sync all my songs with the other computers at home plus my iPhone.
I was surprised that many songs are displayed in gray and they just dont play.
I ma not sure if they were purchased from iTunes or belonged to my original library downloaded from other sources.
iTunes show a message about authorize the machine, but when I try to do it, the sistem says it is already authorized.
What can I do?
Tnx.,

Michael,
Thanks for answering.
I had a lot of songs on my old iMac. Some bought at iTunes, many others imported from CDs and also a couple of old files I cant even remember their origins.
I activated iMatch and aparently it worked perfectly upgrading the files. After that, I enabled iMatch in my new iMac. Again it seemed to work, but when I began to play, some of the songs showed up with a gray cloud symbol instead of the usual black one. So, these songes dont play.
Ill try to run it again from the iMac. Maybe the connection have failled on the way...
Thanks again.

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Cant Play Some Songs in My iMac Downloaded From the Cloud

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