Posted on 2011-10-18
Medium Priority
Last Modified: 2013-12-17
I have an internal RHEL server called gospel on domain cotw. This is on a Windows network w/ an Exchange server (mail.camp-of-the-woods.org).  I need to get application generated emails from my RHEL box to masquerade as coming from my exchange box.
I have attempted the following changes to my sendmail
define(`SMART_HOST', mail.camp-of-the-woods.org)dnl

My resultant email still reflects what's shown below.  Some headers are changed but not the important ones regarding RDNS.  What else can I try?
Microsoft Mail Internet Headers Version 2.0
Received: from mail pickup service by mail.camp-of-the-woods.org with Microsoft SMTPSVC;
       Tue, 18 Oct 2011 13:55:19 -0400
X-SCL: 5 67.76%
Received: from gospel.cotw.local ([] RDNS failed) by mail.camp-of-the-woods.org with Microsoft SMTPSVC(6.0.3790.4675);
       Tue, 18 Oct 2011 13:55:09 -0400
Received: from gospel.cotw.local (localhost.localdomain [])
      by gospel.cotw.local (8.13.8/8.13.8) with ESMTP id p9IHt8YA017253
      for <randy@camp-of-the-woods.org>; Tue, 18 Oct 2011 13:55:08 -0400
Received: (from randy@localhost)
      by gospel.cotw.local (8.13.8/8.13.8/Submit) id p9IHt8sv017252
     for randy@camp-of-the-woods.org; Tue, 18 Oct 2011 13:55:08 -0400
Date: Tue, 18 Oct 2011 13:55:08 -0400
From: Randy Huseland <randy@camp-of-the-woods.org>
Message-Id: <201110181755.p9IHt8sv017252@gospel.cotw.local>
To: randy@camp-of-the-woods.org
Subject: testing
Return-Path: randy@camp-of-the-woods.org
X-OriginalArrivalTime: 18 Oct 2011 17:55:09.0315 (UTC) FILETIME=[138C8D30:01CC8DBF]

Question by:rhuseland
  • 4
  • 3
LVL 81

Expert Comment

ID: 36989501
The only people who would know the path the mail took are those who look at the message headers.

The masquerade deals with altering visible content From: etc.


Author Comment

ID: 36989560
Yea but the problem is Received: from gospel.cotw.local ([] RDNS failed
I need to make gospel.cotw.local turn into mail.camp-of-the-woods.org so RDNS will pass.
LVL 81

Expert Comment

ID: 36989583
Did you update the configuration after adding the parameters as outlined in the link I posted?

Provided the From: and/or Reply-To: address would direct the response to the correct location, I've not seen a reason to do this setup.  At times it could make it harder to troubleshoot/isolate the source of an email even though an individual receiving an email from each source will clearly see the difference i.e. one will have many more Received Lines.
What does it mean to be "Always On"?

Is your cloud always on? With an Always On cloud you won't have to worry about downtime for maintenance or software application code updates, ensuring that your bottom line isn't affected.

LVL 81

Accepted Solution

arnold earned 500 total points
ID: 36989589
Oh, the Masquerade occurs prior to the message being submitted to the Exchange which is the source of the Received header you referenced.  Nothing on the sendmail side can be done to handle this.
You would have to update the RDNS for the IP in question to reflect a different hostname.

Author Comment

ID: 36989960
Hmmm. Not the answer I was looking for. Maybe I'll have to look for another solution.
LVL 81

Expert Comment

ID: 36990310
What is the significance that you are going through all this.
Does your exchange server also has IIS for OWA?
You could have your process submit email via IIS to an ASP/ASP.NET page that will generate the email. i.e. submit the data as a form.
Alternatively, you could use masquerade as you have, but send the message directly versus routing it through the exchange. This way the receiving server will not be able to differentiate whether the sender is the exchange or not, but the headers will clearly have sendmail as the sending app versus an MS SMTP service.

Assisted Solution

rhuseland earned 0 total points
ID: 37002122
Basically "fixed" it by forcing a change to my Received header in my sendmail.cf.
LVL 15

Expert Comment

by:Jeff Perkins
ID: 37732237
This question has been classified as abandoned and is closed as part of the Cleanup Program. See the recommendation for more details.

Featured Post

Free Tool: SSL Checker

Scans your site and returns information about your SSL implementation and certificate. Helpful for debugging and validating your SSL configuration.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

I have written articles previously comparing SARDU and YUMI.  I also included a couple of lines about Easy2boot (easy2boot.com).  I have now been using, and enjoying easy2boot as my sole multiboot utility for some years and realize that it deserves …
Mailbox Corruption is a nightmare every Exchange DBA wishes he never has. Recovering from it can be super-hectic if not entirely futile. And though techniques like the New-MailboxRepairRequest cmdlet have been designed to help with fixing minor corr…
Sending a Secure fax is easy with eFax Corporate (http://www.enterprise.efax.com). First, just open a new email message. In the To field, type your recipient's fax number @efaxsend.com. You can even send a secure international fax — just include t…
The Email Laundry PDF encryption service allows companies to send confidential encrypted  emails to anybody. The PDF document can also contain attachments that are embedded in the encrypted PDF. The password is randomly generated by The Email Laundr…
Suggested Courses
Course of the Month9 days, 22 hours left to enroll

571 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question