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So one working solution to an authorized song, on an authorized computer, that constantly requests authorization, is to delete that one song, go back into iTunes and purchase it again.
IF there are hundreds of these songs, this would obviously be a painstaking process. What can be done to do a more wholistic fix?
Mac mini, macOS 10.15
I may be wrong, but I believe following the advice in bold reduces the incidence of this problem. You're still going to have to fix any broken tracks by a slow process of discovery.
Repeated requests to authorize an already authorized computer for recent store downloads typically indicates you have corrupt or incomplete copies. Delete the tracks that won't play from your library without hiding from your purchase history. Redownload using the cloud links that should remain, or close iTunes and reopen if they don't show up straight away. While downloading click the activity widget and turn off the option that allows for simultaneous downloads.
If that hasn't helped see If iTunes prompts you to authorize your computer when you try to play iTunes Store purchases - Apple Support.
tt2
I may be wrong, but I believe following the advice in bold reduces the incidence of this problem. You're still going to have to fix any broken tracks by a slow process of discovery.
Repeated requests to authorize an already authorized computer for recent store downloads typically indicates you have corrupt or incomplete copies. Delete the tracks that won't play from your library without hiding from your purchase history. Redownload using the cloud links that should remain, or close iTunes and reopen if they don't show up straight away. While downloading click the activity widget and turn off the option that allows for simultaneous downloads.
If that hasn't helped see If iTunes prompts you to authorize your computer when you try to play iTunes Store purchases - Apple Support.
tt2
authorized song will not play on authorized computer
