Hi, I was monkeying around a bit with s_client. Idea is to feed s_client a file with commands required to STARTTLS, authenticate to the smtp server and the message itself. I have this file:
------------------------------ ehlo hereami auth login dfbdffdbZWhhcjU= dffbbbbdddBoYTI= mail from:<here...@gmail.com> rcpt to:<here...@gmail.com> data From: <here...@gmail.com> To: <whoe...@gmail.com> Subject: With s_client Date: Mon, 18 Feb 2013 22:28:00 +0100 Testing ... ______________________________________________________________________ OpenSSL Project http://www.openssl.org User Support Mailing List openssl-users@openssl.org Automated List Manager majord...@openssl.org