TEST.proto.SMTPAUTH

The stuff in bold is what you have to do. The rest is output you should see

Notes

• In the first perl command, you need to put the \000 in there and the comment for the @ symbol
• Don't forget to wait for the banner
• Use the output you get from the perl command to derive your AUTH PLAIN argument
• Optionally test port 25, it should work there as well

Sample SMTP Session - AUTH PLAIN

• perl -MMIME::Base64 -e 'print encode_base64("\0bob.miller\@computerisms.com\0XXXXXXXX");'
  AGJvYi5taWxsZXJAY29tcHV0ZXJpc21zLmNvbQBGcjEzZDNnZ3M= <= Highlight/Copy this output
• openssl s_client -starttls smtp -crlf -connect 192.168.26.10:587
• CONNECTED(00000003)
• <snip> Lots of Certificate Information </snip>
• ---
• 250 8BITMIME
• ehlo computerisms.ca
• 250-computerisms.com I am the Computerisms Mail Server. I do not relay unauthorized messages. I actively refuse spam. All other messages are welcome.
• 250-PIPELINING
• 250-SIZE 10240000
• 250-DATAZ
• 250-AUTH LOGIN PLAIN <= Note: this cannot succeed if AUTH PLAIN is not advertised
• 250 8BITMIME
• AUTH PLAIN AGJvYi5taWxsZXJAY29tcHV0ZXJpc21zLmNvbQBGcjEzZDNnZ3M= <= Note: Paste this value from your clipboard
• 235 nice to meet you
• mail from: <bob.miller@computerisms.com>
• 250 ok
• rcpt to: <bob.miller@computerisms.com>
• 250 ok
• data
• 354 go ahead punk, make my day
• Subject: test
• test
• . <= Note: The dot by itself indicates end of message, it needs to be here
• 250 ok 1375486500 qp 4151 by computerisms.com
• quit
• 221 computerisms.com Goodbye.