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Sendmail header issue

Sendmail header issue

I'm having a problem with some documents sent from my server via sendmail not getting through. This only happens with certain destinations and I believe it is related to some sort of spam filtering before the mail gets to the destination domain.

The mail header looks like this

Microsoft Mail Internet Headers Version 2.0
Received: from earth.mydomain.com ([172.20.20.201]) by myexchangerelay.corp.mydomain.com with Microsoft SMTPSVC(6.0.3790.3959);
Tue, 10 Feb 2009 08:35:08 -0500
Received: (from user@localhost)
by earth.mydomain.com (8.9.3 (PHNE_29774)/8.9.3) id IAA01463;
Tue, 10 Feb 2009 08:35:07 -0500 (EST)
Date: Tue, 10 Feb 2009 08:35:07 -0500 (EST)
Message-Id: <200902101335.IAA01463@earth.mydomain.com>
From: autoprocess@mydomain.com
To: customer1@hisdomain.com
MIME-Version: 1.0
Content-Type: multipart/mixed;
Subject: Shipment
Content-Type: text/html
Return-Path: user@mydomain.com
X-OriginalArrivalTime: 10 Feb 2009 13:35:08.0082 (UTC) FILETIME=[63AA5120:01C98B84]

I think the problem is the received from address at the top says @localhost and the return-path says @mydomain.com.

I'm using a DM rule to masquerade mydomain.com and have Dj$w.mydomain.com set as well.

My DS relay is using the local name for my exchange server and this part of the set up has been working for years.

My question is, how do I get the initial Received: (from user@localhost) to show my DM domain?



7 REPLIES
VK2COT
Honored Contributor

Re: Sendmail header issue

Hello Patrick,

I do not think your headers are the problem.

a) "Message-Id", "From" and "Return-Path" are
very consistent and correct:

Message-Id: <200902101335.IAA01463@earth.mydomain.com>
From: autoprocess@mydomain.com
Return-Path: user@mydomain.com

b) The "Received" headers of any email
message tell you where the message
originated and what route it took to get
to you.

Read "Received" headers in reverse order.
The sequence from the last "Received" header
in the message's headers - the one furthest
down in the headers, which is in fact the
first "Received" header that was added to
the message to the top "Received" header
should take you from the email server where
the message originated, to a local incoming
email server, and finally, to your inbox.
So, it looks OK too:

Received: from earth.mydomain.com ([172.20.20.201]) by myexchangerelay.corp.mydomain.com with Microsoft SMTPSVC(6.0.3790.3959);
Tue, 10 Feb 2009 08:35:08 -0500

Received: (from user@localhost)
by earth.mydomain.com (8.9.3 (PHNE_29774)/8.9.3) id IAA01463;
Tue, 10 Feb 2009 08:35:07 -0500 (EST)

c) You probably need to look at it in depth
at remote sites that reject messages from you.

Is it because of some types of attachments,
or is your SMTP gateway missing PTR-
resource record in DNS, or is your SMTP
listed in some spamming database?

If we knew the details of your SMTP
gateway (real IP address) and
the domain name you use to send messages
externally, we could help you more.

By the way, what does mail.log file
says when you send messages to remote
sites?

Cheers,

VK2COT

VK2COT - Dusan Baljevic

Re: Sendmail header issue

Thanks for the reply.

The administrators at the final receipients site say they don't ever see these pieces of mail hit their server. So our theory was that perhaps they were being turned away or passed to a junk mail folder at some intermediate step in the process.

The e-mails are html formatted shipment or invoice notices. We theorized that perhaps the combination of a relay coupled with the format would trigger false positives in some small portion of spam filters. Our mail logs all appear to be normal.

As it stands, this problem affects fewer than 5 out of more than a thousand documents sent each week and only 2 partners out of hundreds, so I'm not sure how much further I want to pursue it.

I thought perhaps it was something someone had seen before.

Thanks for your help.
VK2COT
Honored Contributor

Re: Sendmail header issue

Hello,

If they never get the messages, then
check your /var/adm/syslog/mail.log.
There must be entries about each
message delivered locally or
forwarded to remote sites.

What does the log file says? Who
receives those "undeliverable"
message in the first hop from your server?

Cheers,

VK2COT
VK2COT - Dusan Baljevic

Re: Sendmail header issue

The mail.log just shows the handoff to the mail relay.

Feb 2 14:59:10 earth sendmail[24826]: OAA24799: to=cust1@hisdomain.com ctladdr=userwhoranprocess (312/101), delay=00:0
0:01, xdelay=00:00:01, mailer=relay, relay=relayhost[172.20.20.94], stat=Sent (2.
6.0 <200902021959.OAA24799@earth.mydomain.com> Queued mail for delivery)

I'm starting to wonder if maybe this has something to do with the way MS Exchange is handling the relay
Dennis Handly
Acclaimed Contributor

Re: Sendmail header issue

>I'm starting to wonder if maybe this has something to do with the way MS

Instead of the saying "Nobody expects the Spanish Inquisition!", I thought it was "Always suspect Windows"? :-)
VK2COT
Honored Contributor

Re: Sendmail header issue

Hello,

Now we know what the next step is.

I am sure Dennis and I agree - get rid of
Microsoft Windows.

I made that decision 23 years ago :)
Joke aside, why I like Unix and Linux -
because of freedom to make choices!

I am not locked into any solution, any vendor, there are many choices and
I can modify code for just about anything
if I wish :)

Check server 172.20.20.94 and see what
happens with your message once it gets there.
I would not be surprised if Windows admin
comes back to you and says that they do not
keep email logs :) One major ISP here
in Australia said exactly that to me when
I was investigating a problem for a customer.

Good luck,

VK2COT

VK2COT - Dusan Baljevic

Re: Sendmail header issue

Thanks again for all tha advice. Unfortunately, I can only control what the *IX boxes in our shop do.

Which leads me to this. I use postfix on my redhat boxes and messages sent via it make it through just fine.

Is there an alternative to Sendmail for relaying mail like this?