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Excahnge Server 2013 - Messages from single domain outside organization not making it to exchange server

Posted on 2014-04-11
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Last Modified: 2014-04-17
I have an Exchange 2013 mail server (ourdomain.com) and am having an issue with a single domain outside our organization (outsidedomain.com) that we cannot receive mail from.  When the user from outsidedomain.com replies to one of our emails or initiates an email to one of us, it is never received.  Here is some info on our setup.

Untangle gateway utilizing the spam blocker lite module based on spam assassin technology.  I have globally whitelisted the  outside domain using *@outsidedomain.com wildcard.  When I check the logs, I can see the message gets passed through this SPAM filter on the gateway indicating a global exception so this exception appears to be working.

Exchange 2013 server has message filtering enabled and also has a whitelist entry for the domain in question set by utilizing the set-contentfilterconfig -bypassedsenderdomains cmdlet.  I have verified that the domain shows as an exception when I run get-contentfilterconfig.  I have temporarly set the -SCLrejectenabled and -SCLdeleteenabled settings to $false for troubleshooting purposes.  -SCLQuarantineenabled is sill at $true but the messages never make it to the quarantine box.  

Steps I have taken to find any trace of this message in exchange 2013:
I contacted user at outsidedomain.com and requested she send an email to my test mailbox.  I see the mail item get marked as passed via global exception on the untangle spam filter.  
I open the EMS and run the get-messagetrackinglog -recipients "test@ourdomain.com" -start "4/11/2014 8:00AM" -end "4/11/2014 {current time}" cmdlet and will get nothing.
Run cmdlet get-messagetrackinglog -sender "user@outsidedomain.com" -start "4/11/2014 8:00AM" -end "4/11/2014 {current time}" and get nothing.
Run cmdlet get-messagetrackinglog -start "4/11/2014 8:00AM" -end "4/11/2014 {current time}" -eventid "fail" and will see some questionable messages, but not any from @outsidedomain.com.  Attempted other eventid types like "poisonmessage" "badmail" etc and did not see it there either.
Checked SPAM quarantine mailbox on exchange and message has not been quarantined.

 Since I can find no trace of the mail items from user@outsidedomain.com on the exchange server, it almost feels like the untangle gateway is doing something with the mail item that causes it to not make it to exchange, but according to the gateways logs it is passing the message.  I also ran the Exchange remote connectivity analyzer and it had no problems with the inbound SMTP test.  Any thoughts or troubleshooting steps you guys have would be greatly appreciated.
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Question by:nylex
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Simon Butler (Sembee) earned 500 total points
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Enable logging on the receive connector and see if the messages are listed there. You need to confirm they are being received by Exchange.

Simon.
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Author Closing Comment

by:nylex
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Thanks for the feedback Simon.  I ended up working with the outside user and found I could receive mail from her webmail and phone...the issue was with the SMTP server on her outlook client.  Still not sure why it wasn't getting to Exchange, but after having her update her SMTP server I now can.  If I have an issue like this int he future I will definitely try logging the receive connector.  Tanks for the advice and since you are the only one who replied, you get ALL THE POINTS!
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