generate User and Password Hashes
echo -n 'username or password' | openssl base64
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
caveats:
- Password hash should not start with a "R":
https://www.openssl.org/docs/man3.0/man1/openssl-s_client.html R: Renegotiate the SSL session (TLSv1.2 and below only).