Emails Sent from one computer are received, from another they are not
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?
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?
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.
ASKER
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.
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.
ASKER
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.
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.
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.
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.
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.
ASKER
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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ASKER
Not very definitive.
Do you only have one (outside) static ip in your org, or multiple?