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Emails Sent from one computer are received, from another they are not

Posted on 2011-10-17
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Last Modified: 2012-11-21
This ranks as one of the strangest things I have seen in many years of working with Outlook and Exchange and therefore truly worthy of 500 points!  

In trying to email a legitimate email address at myfairpoint.net, emails get through from Computer A.  From Computer B, emails to the same myfairpoint.net address vanish into thin air (they are never received, they never bounce).  It's clear from the logs of our Smarthost provider that both sets of emails properly leave our server and properly leave the Smarthost's server, but the results are entirely different.  Obviously Fairpoint is treating the emails from Computer A differently than emails from Comptuer B, but what could possibly be different?  

And the behavior of Computer B is identical a third computer tested (Computer C).  And yet Computer A has no problem.  

In all cases, the same domain login account/Exchange Mailbox are used (with results duplicated using a second domain login account/Exchange Mailbox), and the programs in use are identical (Outlook 2007).  The environment is Windows Small Business Server 2008, which uses Exchange 2007.  

I'm going nuts trying to discover what could be different between the successful computer and the not-successful computers.  Since there is no bounce created, I have no message header information to examine for the unsuccessful messages.  I do have the message header information for successful messages, of course.  

Does anyone have any idea whatsoever???  I did notice that the ethernet adapters on the "not successful" computers are node type "Broadcast" and on the comptuer which is successful it is node type "Hybrid."  I can't imagine that has anything to do with anything, though.  

Can anyone help?        

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Question by:PCoffinFMI
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LVL 7

Expert Comment

by:mikeewalton
ID: 36983797
Just to clarify, you are using the same exchange account to send from both pc A and B?

Do you only have one (outside) static ip in your org, or multiple?
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LVL 11

Expert Comment

by:Sigurdur Haraldsson
ID: 36984452
Do the missing emails arrive at Fairpoint at all? Let them check their logs to see if they receive them and how they handle them after that, if they arrive. If they don't arrive, you'll have to trace it from hop to hop with your ISP.
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Author Comment

by:PCoffinFMI
ID: 36985656
To mikeewalton -

Yes, the same Exchange account from both PC A and B.  Not only that, but two DIFFERENT Exchange accounts behave the exact same way.  

Yes, the organization has only a single outside static IP address.  The only test that IP address fails on MXTOOLBOX is reverse lookup.  I have asked the ISP to correct the PTR record.  However, I'm told that use of reverse DNS lookup is unusual for spam filtering these days, and since all mail leaving the organization leaves the same way the question of why mail from Comptuer A gets through and mail from Comptuer B does not is still there.  

To sighar -

I don't know if the missing emails reach Fairpoint.  I don't have an easy way of communicating with them but I suppose that's the next step.  The situation is that the myfairpoint email address belongs to one of the executives at her home so in seeing this behavior it's convinced her that a lot of other outbound mail isn't getting out, which does not seem to be the case, actually - but it's hard to know that for sure.  So I would have to ask an already-agitated exec for their account info in order to call Fairpoint.  But it may come to that, I do see what you're saying.  
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Author Comment

by:PCoffinFMI
ID: 36985669
Clarification to Sighar -

In my reply to your question, I should not have used the phrase "mail not getting out" - I shoudl have said "mail not getting delivered to the fairpoint email address"  - mail is definitely getting out, I can see that clearly in the Smarthost logs.  
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Expert Comment

by:Sigurdur Haraldsson
ID: 36985775
Yep, that's why I suggested tracking from the other side. It´s quicker to see if the problem is there or somewhere on the way.
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Expert Comment

by:mikeewalton
ID: 36987475
Can you try sending an email from the PC with the issue through SMTP cmd line?

Obviously you will need to (if blocked) open that pc through your firewall for port 25 temporarily.

There  is a good chance it will possibly show you the error, especially since the issue is looking like it's most likely on their end.
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Author Comment

by:PCoffinFMI
ID: 37008546
Mikeewalton your suggestion is probably a good one but yesterday when I was at the client site I wasn't able to grab any time on either of the two PC's that won't send the emails - unfortunately the PC's belong to two of the busiest users at the client.  So I will try to do this remotely or worst case I will be back onsite mid next week.  Thank you for the suggestion.  
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Accepted Solution

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PCoffinFMI earned 0 total points
ID: 38605749
Just to follow-up, the e-mail behaviors could never be fully explained, but ultimately the customer was changed-over to an SMTP smarthost service for outbound email and these issues went away.  Apparently whatever filtering this customer was subject to varied by factors which involved the individual computers sending the emails, not just the sending domain (which still makes no sense to me).  No clear answer here except for the general observation that a clean SMTP smarthost can definitely help to solve strange email sending problems.
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Author Closing Comment

by:PCoffinFMI
ID: 38619991
Not very definitive.
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