For anyone who wants to try this against a modern server:

    openssl s_client -connect smtp.mailserver.com:smtps -crlf
    220 smtp.mailserver.com ESMTP Postfix (Debian/GNU)
    EHLO example.com
    250-smtp.mailserver.com
    250-PIPELINING
    250-SIZE 10240000
    250-VRFY
    250-ETRN
    250-AUTH PLAIN LOGIN
    250-ENHANCEDSTATUSCODES
    250-8BITMIME
    250-DSN
    250-SMTPUTF8
    250 CHUNKING

    MAIL FROM:me@example.com
    250 2.1.0 Ok

    RCPT TO:postmaster
    250 2.1.5 Ok

    DATA
    354 End data with <CR><LF>.<CR><LF>

    Hi
    .
    250 2.0.0 Ok: queued as BADA579CCB

    QUIT
    221 2.0.0 Bye