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I have certificates x.509 for signing and enrypting outgoing emails. I want to create plain emails in some app (Ruby on Rails app in my case) and send it via sendmail with autosign and autocrypt solution.

Is it possible?

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You should be able to do this using a milter such as MIMEDefang:

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I tried to find documentation how to sign emails automatically, but failed. I'm new in this area. Do you have such tutorial? – petRUShka Jun 30 '11 at 16:27

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