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bsimmons2376

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How do I troubleshoot web generated email not being received by certain users?

I am having a wierd email issue that I need assistance with.  I am going to use domain.com in place of our actual domain name for my question.  When someone registers on our website for our PMI training, certain users are not receiving the registration emails.  When someone registers for a class,  our Training mailbox is supposed to receive the email plus the person who registered.  I have a mailbox setup on our Exchange server with training@domain.com as it's email address.  Our training mailbox never receives the email,but the person who registered does.  Here is our setup:
-  Website is hosted with Server Intellect.  Website is setup to send (or pretend to send)registration email from training@domain.com to training@domain.com and registereduser@differentdomain.com.  The web developer that setup our training pages also has bill.burkard@domain.com (who is one of my users on our Exchange server) being bcc'd on the registration emails.  What's strange is that Bill gets them??  When the email is generated, the web developer has the FROM coming from training@domain.com.
-  Our domain is registered thru GoDaddy.  Our domain is pointed to the nameservers at Server Intellect.
-  Our internal active directory domain is the same as our external domain
-  We use an internal Exchange 2007 server.
I checked the message tracking logs on my Exchange server.  I performed a filter on email coming from training@domain.com  It found the registration emails that bill.burkard@domain.com received.  It's as if our website is using my internal Training mailbox to send the email, but the IP it originates from is the IP of one of our nameservers at Server Intellect.  I verified this by looking at our external DNS settings.  I also have a SPF record setup for our domain.  Just for laughs, I tested adding the IP our website was using to send the email to our SPF record, but that didn't work.  Is it a DNS issue, SPF record issue, Exchange server issue, or how our website is generating the email.  What is very confusing is if bill.burkard@domain.com is getting the emails, why isn't training@domain.com receiving the emails.  I am desperate for any help.  It is very important that we get this working.

Thank you!!
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icfire

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Hi, do you have an anti-spam firewall?

If so then add training@domain.com to the whitelist  

If you are using exchange to do it the use this:

Using EMS, try the following:
set-contentfilterconfig -BypassedSenders training@domain.com

Here's a couple blogs worth reading
http://exchangepedia.com/blog/2007/01/exchange-2007-content-filter-whitelist.html

http://exchangepedia.com/blog/2007/02/how-to-update-multi-valued-attributes.html

HTH
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bsimmons2376

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I am using Trend Micro Scanmail for Exchange as our spam filter.  I added training@domain.com to the whitelist and made sure all the anti-spam agents on the Exchange server were disabled.  I tested registering and I still didn't get the email at training@mts-usa.com  
When I registered I used my gmail account and I received the registration email there just fine, which has been working.  I did look at the message source on the email that I received at my gmail account and found something interesting.  I have attached that portion of the message source here (again, domain.com is substituted for our actual domain):
Return-Path: <training@domain.com>
Received: from mail.si-sv2217.com ([74.86.36.69])
        by mx.google.com with ESMTP id 8si15688141gxk.15.2009.02.25.14.17.44;
        Wed, 25 Feb 2009 14:17:44 -0800 (PST)
Received-SPF: softfail (google.com: domain of transitioning training@domain.com does not designate 74.86.36.69 as permitted sender) client-ip=74.86.36.69;
Authentication-Results: mx.google.com; spf=softfail (google.com: domain of transitioning training@domain.com does not designate 74.86.36.69 as permitted sender) smtp.mail=training@domain.com

Could it have something to do with our SPF record?  But then again, bill.burkard@domain.com is still receiving the registration emails.  His account and the Training account are setup the same way on my Exchange server.  I don't get it.  I am going to try what icfire suggested.

Thanks for any help!!!
I goofed and gave out our domain.  Oh well.  :-(
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MightySW
When you say exclude training@domain.com, do you mean add that to my SPF record so that it is an accepted source for email.  Would I just add it as a hostname to the SPF?  
To answer your question, the user that was getting the email from our website was being bcc'd.
I'm confused about that - if he is getting it, why isn't my Training mailbox getting it.  Would it still be the SPF record?

Thanks for your quick response,
Yes, it should be an accepted source of email.  Do not add just domain.com, but just add the user and training@domain.com.  I know that the BCC works, but you should add it JIC.

Also, for grins, do a BCC to training@domain.com also.  If it goes is this acceptable?  This way you keep the integrity of your SPF record without allowing potential spoofs.
Hey,
I figured out it wasn't anything on my end.  The web developer did not have the registration emails sending to training@domain.com.  She only had it setup to bcc one of my users.  Something that was just overlooked.  She has now added training@domain.com in the TO field and it is working.  Thanks to both of you for your comments.  Very informative even though i ended up not needing them.

Thanks again
awesome job.