This seems to be one of the greatest mysteries to new postmasters. It can be confusing as the messages go to the SMTP MAIL FROM address, which can be different from, or the same as the from header. If you’re reading this article, we would first suggest reviewing the article, “How to check an SMTP connection with a manual telnet session” as it covers the basics of the SMTP dialog.

The key to understanding bounces (sometimes referred to as DSNs, Delivery Status Notifications or NDRs, Non-Delivery Reports) is that they should always be sent to the SMTP MAIL FROM address. Some mail platforms may not adhere to this rule, but most do, so we’ll focus on the majority of what you’re likely to see. From review of the above mentioned post, there is the following sample SMTP session:

==================START SESSION==================<br /> telnet mail.port25.com 25<br /> Trying 69.63.149.30…<br /> Connected to mail.port25.com (69.63.149.30).<br /> Escape character is ‘^]’.<br /> 220 mail.port25.com (PowerMTA(TM) v4.0) ESMTP service ready<br /> EHLO server.example.com<br /> 250-mail.port25.com says hello<br /> 250-STARTTLS<br /> 250-ENHANCEDSTATUSCODES<br /> 250-PIPELINING<br /> 250-CHUNKING<br /> 250-8BITMIME<br /> 250-XACK<br /> 250-XMRG<br /> 250-SIZE 54525952<br /> 250-VERP<br /> 250 DSN<br /> MAIL FROM: <[email protected]><br /> 250 2.1.0 MAIL ok<br /> RCPT TO: <[email protected]><br /> 250 2.1.5 <[email protected]> ok<br /> DATA<br /> 354 send message<br /> From: “John Smith” <[email protected]><br /> To: “Jane Doe” <[email protected]><br /> Subject: test message sent from manual telnet session<br /> Date: Wed, 11 May 2011 16:19:57 -0400

Hello World,
This is a test message sent from a manual telnet session.

Yours truly,
SMTP administrator

.
250 2.6.0 message received
QUIT
221 2.0.0 mail.port25.com says goodbye
====================END SESSION==================

In the above example there are two from addresses:

MAIL FROM: <[email protected]>

And:

From: “John Smith” <[email protected]>

It is the former, the MAIL FROM address, to which bounces are sent. The latter, the ‘from:’ header, is part of the body of the message and is what shows in the email client as the sender of the message.

Of course, one might ask, how do I check the message to see where the bounces would be sent? This is easily done by checking the full headers of the message. Here are some examples of well known email clients and how to check the headers (assuming you are already viewing the given email in question:

• Yahoo – Click More -> View Full Header
• Gmail – Click the dropdown arrow next to the reply button -> Show original
• Hotmail – Click Actions -> View message source
• Outlook desktop client – Right click on the message and select Message Options
• Mac Mail – Command+Shift+H or View Menu -> Message -> All Headers

Once you have the headers in front of you, they should look something like the following:

From “Scott Habicht” Fri Nov 14 19:57:42 2014<br /> Return-Path: <[email protected]><br /> Received: by mail.port25.com id hcpfbm11u8kk for <[email protected]>; Fri, 14 Nov 2014 14:57:47 -0500 (envelope-from <[email protected]>)<br /> From: “Scott Habicht” <[email protected]><br /> To: <[email protected]><br /> Subject: testing headers<br /> Date: Fri, 14 Nov 2014 14:57:42 -0500<br /> MIME-Version: 1.0<br /> Content-Type: multipart/alternative;<br /> boundary=”—-=_NextPart_000_0075_01D0001B.57BC7570?<br /> Content-Language: en-us<br /> Content-Length: 2066

In the above example, it is very easy to the see the From: header, but what happened to the SMTP MAIL FROM address? Well, it is now shown as the Return-Path header:

The top entry was added by Yahoo: