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I know that by adding/modifying the SubjectAltName entry in openssl.cnf this can be achieved, but is there a way to do so without having to modify that file every time?

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In openssl.cnf at the top add the entry SAN = "email:copy" (to have a default value in case the environment variable SAN is not set) and in the respective section use SubjectAltName = ${ENV::SAN}. Now just call SAN="email:copy, email:adress@two" openssl ..., where email:copy makes sure the main address is used as well. (Adapted from here)

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note to self: If your only access is via SSH, make sure your openssl.conf is valid. The simplest check is trying to establish a second connection (or scp something) without cutting the first one –  Tobias Kienzler Mar 12 '13 at 13:26

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