IO::Socket::SSL has a ->start_SSL method, which will upgrade your "plain" socket to a SSL-encrypted connection. I think this is what all the other things that use StartTLS use (Google Code Search), but if not, maybe you find the appropriate things there. Also, have you looked at what CPAN has to offer for ESMTP, which seems what you're implementing?

In reply to Re: How to enable SSL support in sockets connected with a sock5 server? by Corion
in thread How to enable SSL support in sockets connected with a sock5 server? by dxxd116

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