´´´ # echo -ne "user@example.com" | base64 # dXNlckBleGFtcGxlLmNvbQ== # echo -ne "PutYourSecretPasswordHere" | base64 # UHV0WW91clNlY3JldFBhc3N3b3JkSGVyZQ== openssl s_client -starttls smtp -crlf -connect smtp.example.com:587 EHLO test AUTH LOGIN dXNlckBleGFtcGxlLmNvbQ== UHV0WW91clNlY3JldFBhc3N3b3JkSGVyZQ== mail from: rcpt to: data From: John Doe To: Mary Doe Subject: Test ESMTP Auth LOGIN Testing proves the existence of bugs not their absence . ´´´