Experiments with SMTP LG #45

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1. Introduction

I got a lot of reactions to ‘Setting Up Mail for a Home Network Using Exim’ in LG 43. Most of them said two things:

  • your article was most welcome. I have been struggling with the same problem myself.
  • but I did what you said, and it does not work!

So I went ‘back to the drawing board’ and had a good look at what happens when e-mail is sent. As a result, this article explains what you must do to make the setup in the LG 43 article really work (I think) .. and also why.


SMTP, as you probably know, stands for ‘Simple Mail Transfer Protocol’. It is the method by means of which mail is exchanged between computers on the Internet. Basic communication between computers (exchange of single packets and of streams of information) is provided for by TCP/IP.  SMTP is a protocol ‘on top of’ TCP/IP for exchanging messages between computers. Let’s do a few experiments to see how SMTP works.

A basic tool for making TCP/IP connections is telnet. If you type

telnet host port

your computer makes a connection to a computer named host on port port. It is like making a telephone call to the office of a company called ‘host’ and asking to speak to Mr. Port. Only if Mr. Port is in and willing to talk to you, will the call succeed. Similarly, a program (‘daemon’) must be active on the other computer, ‘listening’ for connections on the specified port, otherwise you will get the message ‘connection refused’.

port is a (16-bit) number. Certain port numbers have been pre-assigned to certain services. Electronic mail (SMTP) uses port 25, and the daemon listening to port 25 is the MTA (the Mail Transport Agent: sendmail, exim, qmail, etc.). If your Linux box is called heaven, you call its SMTP service by typing

telnet heaven 25

You can do this from another computer through a network (LAN or Internet), but you don’t need a network: you can test it also by running telnet from the same computer that the MTA runs on. You can even type

telnet heaven smtp

because telnet finds out what the port number of SMTP is by looking it up in /etc/services. The result will be something like:

Connected to heaven.home.
Escape character is ‘^]’.
220 heaven.home ESMTP Exim 3.03 #1 Sun, 8 Aug 1999 12:47:24 +0200

This shows that I am running exim 3.03 (I recently upgraded from 2.05 for a good reason, see section 5 below). If I telnet in the same way to the mail server of my ISP, I see that they run Sendmail 8.8.8/1.19.

After the line beginning with 220 you see no prompt or anything; the MTA awaits your instructions. What to do next? Try typing help. The reaction is:

214-Commands supported:

These are the commands of the SMTP command language, or ‘protocol’, that are supported by your site. Not a lot of commands! SMTP is really a ‘simple’ protocol. The commands are described in the Internet standard RFC821. Some ‘extended’ commands were added later, in other RFC’s, for instance RFC1869. Systems which recognize the extended commands are said to support ‘Extended SMTP’, or ESMTP. Such systems announce this in their ‘welcoming line’, as Exim 3.03 did above. The differences between SMTP and ESMTP are not great.

To break the SMTP connection, send the QUIT command.

3. Exchanging greetings: the HELO/EHLO command

After the welcoming line (beginning with 220) from the remote system, you are supposed to send commands. The first command should be HELO, or, if you are dealing with an ESMTP system, EHLO, the more modern version. The command should have your domain name as argument:

Lire aussi...  HelpDex LG #55

EHLO yourdomainname

If  you have a home system without an official domain name, what name do you use? In fact anything is OK,  including your own, self-chosen domain name, such as heaven.home. Let’s try it with our ISP’s SMTP server by typing telnet smtp.isp.com 25 or whatever. After the welcome message type

EHLO heaven.home

We  get a more or less elaborate ‘greeting’ message, like:

250-smtp.isp.com Hello customer123.dialin.isp.com [xxx.yyy.zzz.123], pleased to meet you

The greeting begins with ‘250’; this is the SMTP ‘OK’ code. In this case we are also greeted with our temporary domain name (customer123.dialin.isp.com) and temporary IP address (xxx.yyy.zzz.123) that were dynamically assigned to us when we opened the ppp connection. This information is available to the other system from the underlying Internet transport layer (TCP/IP). In the case of an EHLO command, the other system also sends a few ‘250’ lines announcing which extra SMTP or ESMTP commands it understands, apart from the minimum set required by RFC821.

Mail servers generally don’t look at the argument of the EHLO or HELO command at all (‘heaven.home’). That means that in practice the EHLO/HELO transaction always succeeds. If the other system doesn’t want to do business with you, it has already refused the telnet host smtp connection.

4. Sending the mail

By just a telnet host smtp connection to a mail server you can send electronic mail ‘by hand’, without even using an MTA or a mail user program like pine. Let’s try this (for safety’s sake) within our own network at first; in this case of course, we must have a mail server (MTA) running.  User joe sends a message to user emi. This involves three steps. First the MAIL FROM: command (SMTP commands are not case sensitive, so you could also type mail from:).

MAIL FROM: joe@home
250 is syntactically correct

We get a ‘250’ line as answer, so this is OK. Now the second step: the RCPT TO: command, specifying who will get the message.

RCPT TO: emi@home
250 is syntactically correct

So this is also 250, OK. The third step: we enter the message itself, using the DATA command:

354 Enter message, ending with « . » on a line by itself

The ‘354’ reply invites us to type the message data. This is not only the text (or ‘body’) of  the message! The ‘message data’ also include the message headers, such as Subject:, To:, Cc:, and From:. The structure of a message is specified in another Internet standard, RFC822. Strictly speaking that is no longer SMTP’s business. SMTP is only concerned with the envelope of the message, that is, the information in the MAIL FROM: and RCPT TO: commands. So, the To: header inside the message and the RCPT TO: address on the envelope of the message are in principle two different things. You can actually make them different (experiment only with local messages please!). So, for instance, after the ‘354’ reply we can type a message with ‘fake headers’:

To: My Daughter
From: Your Dad