I let Thunderbird update itself the other day and then discovered that older versions of GPG, as I was using, were no longer supported. The actual error message said something about not being able to find gpg-agent I downloaded the newest version of GPG tools, but it still didn't work. I found this helpful post and tried to follow the directions, but couldn't seemingly get anything to work.
Eventually, I found that the pinentry-mac.app appears to be broken: even when I downloaded the source and built it myself with xcode, it didn't work. Something has changed about the way the MacOS launches things -- it passes in some process identifier that appears to confuse something. But I didn't know enough about how it works to figure it out.
Eventually, I solved the problem by building plain old pinentry via macports and when I configured gpg-agent.conf to use that pinentry, enigmail just started to work again. Hurray!
- Steven D. Brewer's blog
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