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I have had this happen to me a few times now after starting the IDE. Unfortunately I do not have any reproduction steps. Basically the option is greyed out and you can not click it. It has happened without even loading a Xamarin project. It has also happened after I go to "Tools > Options > Xamarin > iOS" and connected to a Mac agent. I have not checked to see if it is disabled after immediately starting the IDE though.
I will update the bug with more information as I find out more along with logs.
env info: https://gist.github.com/BenBeckley/6cee46340a916674657bd90ebfcb6f14
*** This bug has been marked as a duplicate of bug 53214 ***