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Despite me installing pinentry, I still get the following error:

xxxxxxxMacxxxxx:~ MAU$ gpg2 -c --cipher-algo=aes
gpg-agent[89931]: can't connect to the PIN entry module: IPC connect call failed
gpg-agent[89931]: command get_passphrase failed: No pinentry
gpg: problem with the agent: No pinentry
gpg: error creating passphrase: Operation cancelled
gpg: symmetric encryption of `[stdin]' failed: Operation cancelled
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up vote 2 down vote accepted

It was actually a gpg-agent.conf file left over from when I had mac GPG installed. Oh yeah and here's a test of gpg's symmetric encryption function (the password is stackexchange (all lowercase) btw.):

Version: GnuPG v2.0.20 (Darwin)

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Decrypts fine here. :) Also, nice to see you're using TWOFISH. – Ben Oct 29 '13 at 6:37

When pinentry dies you need to relaunch it from wherever its launch on start instructions get installed to (I'm pretty sure it's somewhere in /System/Library/, but that doesn't really narrow it down). It's possible that "kill -HUP $PID" on the process ID of gpg-agent might kick it into gear too.

Alternatively GPG 1.4.x can exist alongside GPG 2.0.x and is usually compiled without gpg-agent. So it will keep working. I recommend recompiling from source with the current version, though. That's how I've avoided all the pain from gpg-agent.

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I assume you think I'm using the precompiled distrib of gpg for mac osx? I'm using a version I compiled myself. – rake Oct 28 '13 at 21:12
Excellent. Personally I use my own version of the 1.4.x branch (with all cipher algorithms, larger key sizes and increased secmem). If sticking with the 2.0.x branch you should update to 2.0.22 due to a couple of obscure security issues (unlikely to be an issue on your own hardware, but still). – Ben Oct 29 '13 at 6:36

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