SMTP COMMANDS TO SEND EMAILS USING GMAIL

You should understand that this lab will only work if you follow the instructions given to you by your
instructor. You need to setup openSSL and allow your sending email address certain permissions to be
able to send emails from a non-secure client like the terminal.

The commands are in bold.

● openssl s_client -starttls smtp -connect smtp.gmail.com:587

● ehlo gmail.com

● auth login (after giving this command you will receive VXNlcm5hbWU6, which means
‘UserName:’)
● enter your base64 encoded username (after giving this command you will receive
UGFzc3dvcmQ6 which means ‘password:’)
● enter you base64 encoded password.

● mail from: <sender’s email address>

● rcpt to: <recipient’s email address>

● data

● type you email here and when you are done. Enter a (.) on a separate line by itself and hit enter.

● The email will be sent.

YOU SHOULD HAND IN THE FOLLOWING AFTER COMPLETING THIS LAB.

Use wireshark and capture the traffic generated by the commands you have entered and submit the
answers to the following questions.

1. The IP address and TCP port used by the host which is sending the email:
2. The IP address and the TCP port used by the SMTP server:
3. Who is sending the email:
4. Who is receiving the email:
5. When was the email sent:
6. What was the message, and what was the subject of the email:
7. The IP address and TCP port used by the host which is sending the email:
8. See the details of IMAP/POP3 and try to use the openSSL to read emails as well.