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Exchange 2010 email being lost to one external domain

Posted on 2016-09-21
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Last Modified: 2016-10-07
Greetings.

I have an issue where my employees cannot send to a particular external domain.  They receive an email from us on a rare occasion, but others never make it and we don't get any NDR or delay messages.  I've tried doing read and delivery requests, but you can't expect much of those.  I'm not having this with any other domain.  The external domain says that they have added our domain to be safe and have added the IP address of our sending server.  Neither party is on any blacklists.  The attempted recipient states that they don't see any evidence within their AV (I think they said McAfee).  Anyhow, I'm wondering if anyone knows of a site/tool that will allow me to track my outgoing emails?  As I have to trust that the recipient's IT dept know what they are doing, I'm hoping to collect as much info as I can.

Any ideas?

Thanks,

Jeremy
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Question by:Jer
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by:Todd Nelson
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Can you telnet to their mail server(s) on port 25 and send a test message as one of your email addresses to one of their email addresses?

It might be interesting to see what error or message comes up--or does not.
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Simon Butler (Sembee) earned 250 total points
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Message Tracking on Exchange will tell you what Exchange did with the message, including the delivery of the email. If it was delivered to their server then that is as much as you can do.
If it was delivered to another server then you would need to find out what that server is. However once the email has been delivered to a server outside of your control, you are pretty much stuck.

I expect the other side is dropping your email for some reason - probably within their spam filtering service. While whitelisting should help, it depends if the problem is elsewhere. Unfortunately only the recipient can resolve this.
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by:Jer
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Yeah, telnet fails and tracking simply states that the message was successfully handed off to a different e-mail system.  I was just hoping there may be another tool that may interact with the receiving server.  I just don't have a lot of confidence in the IT staff on their end.  They sound like they know the basics of their email environment and that is it.  Well, I'll keep working with them.  Thanks for the feedback.
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by:Todd Nelson
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Unfortunately, once there is a handoff from your organization to the recipient's, there isn't much insight to where the message goes or what happens to it.

But you can take the telnet info to them to show proof from your side.

Good luck and let us know what the outcome is.
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by:Todd Nelson
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Jer,

Will you provide a status update for us?
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by:Jer
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As expected, the issue was on the recipient's side.  Apparently, 1 of our public IP addresses were being blocked their Barracuda solution.  As such, this apparently blocked other IPs in the block.  I never actually was able to get specifics.  Since they 'corrected' the matter, our emails have flowed without issue.
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Author Closing Comment

by:Jer
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Thanks for the feedback, guys.  Sorry for being tardy on the closing of the ticket.
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