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


  • 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\\0XXXXXXXX");'
    AGJvYi5taWxsZXJAY29tcHV0ZXJpc21zLmNvbQBGcjEzZDNnZ3M= <= Highlight/Copy this output
  • openssl s_client -starttls smtp -crlf -connect
  • CONNECTED(00000003)
  • <snip> Lots of Certificate Information </snip>
  • ---
  • 250 8BITMIME
  • ehlo
  • I am the Computerisms Mail Server. I do not relay unauthorized messages. I actively refuse spam. All other messages are welcome.
  • 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: <>
  • 250 ok
  • rcpt to: <>
  • 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
  • quit
  • 221 Goodbye.