The best place to run Telnet is on the server which sends out your SMTP traffic. This will show you the same information that your SMTP engine receives when communicating with an outside system. Telnet allows you to specify the port through which to communicate. SMTP is defined as TCP port 25.
Open a command prompt window. Determine the FQDN or the IP address. If you need to determine this information, you can use NSLookup if you know the SMTP domain name you are attempting to connect to. For more information about this, read this article.
At the prompt, type telnet fqdn 25
If the receiving server is accepting SMTP communications, it will respond with an acknowledgement message indicating it is ready to receive your transmission. The acknowledgement should also indicate if it understands SMTP or ESMTP.
Type ehlo testdomain.com
There are two established protocols, SMTP and ESMTP (Enhanced SMTP). If the receiving system only understands SMTP, you must begin with helo. If the receiving system understands ESMTP, you may begin with either helo or ehlo.
If you receive an OK message from the receiving mail system, proceed. If not, double check the protocol named in the response to the telnet command.
This indicates the reply address. Some receiving systems will compare the parameter from the ehlo command, and the domain listed in the address on the mail from: command to the domain name returned when performing a reverse DNS (RDNS) lookup on the IP address from which the message is coming. It is a method to combat address spoofing and more reliably identify undesirable senders.
If you are testing communications to an outside messaging system, you may need to use your actual domain name to be allowed to continue.
This indicates the recipient address. If receivingdomain.com is not a domain being fielded by the receiving system, and the system does not allow relaying to receivingdomain.com, an error code will be returned.
This begins the actual message. Optionally, From:, To:, and BCC: can be entered at this time (to be covered in a future article).
Type subject: Test message via Telnet
Type a blank line - this denotes the end of the subject and the beginning of the message body.
Type This is a test
Type Please reply if received
Type a blank line
Type a period (".") and press Enter - this marks the end of the message body. The receiving system will understand and return a prompt.
This ends the Telnet session and you will be returned to the OS prompt.
If everything has gone well, the message will be on its way to the recipient address. Give it a minute and check. You now know how to manually create and send an SMTP message! This can be a great troubleshooting tool, as you will receive reponses and acknowledgements from the receiving system that can aid in diagnosing a communication problem.