How do i upgrade songs to itunes plus

Question

I have purchases that are DRM-protected that I would like to upgrade to DRM-free. Searching help here says to go to the iTunes store and 'follow onscreen directions' to upgrade them them to DRM-free. There are no options for doing this.
Can someone please tell me if this can, in-fact, be done and, if yes, why on earth is it so hard to find out how???

Answer 1

So I have been messing this problem for a couple days now. And after reading all the different posts concerning this I don't think it will ever be fixed so when it comes to renew match again I wont be. But hopefully with my messing around someone else might be able to get futher with it then I did.
After renewing match I started having this problem. Could have come up sooner then that not sure but didn't get around to using it again after renewing it and was trying to clean up my music since I got a new pc for xmas.
There as some songs, that don't show a purchase date, but very few that don't work that show they should play and are available to download that just don't work at all.
But most that don't work, prob 90% or more, are purchased songs from itunes and show their purchase dates. They are songs that were eaither upgraded from their DRM versions when that itunes system was avaiable or ones I repuchased.
Im just going to give an example because I think it will be simpler to explain it that way.
I have Gravel Pit in my itunes 2 times...
Gravel Pit, Album = Wu - Tang Clan's Greatest Hits,  iCloud Status = Matched, Purchase Date = 3/13/2006 - DRM version that was download when using the purchased link in the iTunes store.
Gravel Pit,  Album = Wu - Tang Clan's Greatest Hits, iCloud Status = Purhased, Purchase Date = 12/8/2011 - This version wont download or play, the none DRM version.
Now if I go delete the DRM version that shows matched in my folder and open and close iTunes a few times till the download icon reapears song purchased on 3/13 and redownloaded it, I will get the none DRM version I purchased on 12/8/2011. But the download link for the 12/8/2011 still would not work.
Now if that is the actual issue with it or if there are other underling problems I don't know. But maybe someone else will be able to get futher with the issue then I did. Personally I'm just going to give up download what I can of any missing files and cut my loses and tell friends and fam not to get match its just not worth the headache.