Sending TLS mail to Exchange from the command line

Before we look at sending TLS mail to Exchange, let’s talk about using a command line to send mail without TLS.

The command you use to send plain email to Exchange is the telnet client.  It is no longer installed by default but you can install it by adding the Windows Feature for telnet client.  Once it is installed then you can use the following command

telnet serverfqdn 25

Exchange SMTP TELNET

The first thing you need to run after you connect is EHLO or HELO to tell Exchange who you are.  Although Exchange doesn’t really care about what name you give it, the normal name to give is your Fully Qualified Domain Name.

EHLO mypc.me.com

Exchange SMTP EHLO

What you do next depends on the options that Exchange has given you.  There should be one option that starts with 250-AUTH, now if it says LOGIN after that then you can use basic authentication, whereas if it says NTLM then Exchange expects NTLM authentication.  You can also try to send mail without performing any login, although usually Exchange will reject this unless your source IP address happens to be trusted for anonymous mail delivery.

Assuming that Exchange contains LOGIN on the 250-AUTH line then let’s perform a basic authentication login.  Please NOTE that we are NOT using TLS and therefore these credentials could be intercepted on the network.  Exchange expects the username and password to be Base64 encoded, this is to ensure that any special characters won’t interfere with the command syntax.  In order to Base64 encode a phrase you can go to http://www.webpan.com/Customers/Email/base64_conversion.htm

AUTH LOGIN
<type the base64 for your domain\username>
<type the base64 for your password>

Exchange SMTP AUTH

If all has gone to plan then Exchange should now say 235 2.7.0 Authentication successful.  Right so we’re now ready to actually send the email!

First you need a from address, you need to have rights to send from this address, or Exchange needs to be configured to trust you to send as any sender.

MAIL FROM:someone@somewhere.com

Exchange SMTP MAIL

Next you need one or more recipients, the people who will actually get this email.  Exchange needs to know about these recipients or needs to be configured to allow you to relay to any recipient.

RCPT TO:someoneelse@somewhere.com

Exchange SMTP RCPT

That’s the message envelope sorted, now for the actual email

DATA

We’re now ready to type the email itself, this can be just the message body as well as any other headers including

• Date:
• From:
• To:
• Reply-To:
• CC:
• BCC:
• Subject:

If you want to send headers and a message body then type the headers one line at a time first, then a blank line before starting the message body.  At the end of the email enter a . on a line by itself and Exchange will process the message.  If all is well then you’ll get a response code 250 2.6.0 Queued mail for delivery

Exchange SMTP DATA

QUIT

Exchange SMTP QUIT

Right so you may now think, ok well there are loads of tutorials about how to send telnet mail, but if I type STARTTLS after the EHLO then I can’t ever get any further…  That’s true however I wanted to give a quick summary of how you use the basic SMTP commands.  You can use all of the above with TLS mail too, the trick is to not use telnet but openssl to first create the connection.  You can download openssl from www.openssl.org

To use openssl to start a TLS connection use the following command

openssl s_client -connect serverfqdn:25 -starttls smtp

Exchange SMTP TLS

Now you can further add switches like -ssl3 -tls1 -tls1_1 -tls1_2 in order to force openssl to use a specific encryption protocol, so it is great for checking if your server is protected from vulnerabilities like POODLE and BEAST, etc.

Anyway, I hope that is useful to people.  Have fun!