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I love the mutt option crypt_opportunistic_encrypt. This allows me to automatically encrypt emails to recipients for whom I have the key. (And not if I cc to a group that contains members without keys.)

However, I'd also like to automatically sign emails that I encrypt. IMO, if a recipient doesn't use PGP generally, I wouldn't encrypt, and signing would just be noise to them. However, if they do use PGP generally, I'd encrypt and sign by default. Is there a way to do this in mutt?

I looked at crypt_autosign, which signs to all, and crypt_replysign and crypt_replysignencrypted, which only deal with replied emails.

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I had the same problem, the solution I found is:

send-hook . 'reset pgp_autoencrypt'
send-hook "!~l ~t onemail@example\\.org" "set crypt_autoencrypt crypt_autosign"

to automatically encrypt messages to specific recipients, where !~l pattern is to not activate encryption if the mail is also addressed to a known mailing list, and ~t addr means "To: addr".

Note that send-hook is matched against all messages: new and replies.

Some references:

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    I used to do something similar, but (as hinted in the question) the problem is that it works poorly for emails to multiple recipients. If you have a key for only one recipient, mutt will still try to encrypt (and sign) to all. crypt_opportunistic_encrypt avoids this problem, by not encrypting in this case.
    – Sparhawk
    Jan 5, 2017 at 2:19

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