SMTP via openssl an Exchange Server

generate User and Password Hashes

perl -MMIME::Base64 -e 'print encode_base64("username or password");'

openssl s_client -connect mail.example.com:465 -starttls smtp -crlf -ignore_unexpected_eof

EHLO mail.example.com

AUTH LOGIN

username hash

password hash

MAIL FROM:<info@example.com>

rcpt to:<rcpt@example.com>

DATA
Subject: An intresting subject

Some random Email content

.
QUIT