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Email to Exchange servers doesn't get to mailbox

Hi!

I have an organization with a single domain and 2 exchange servers-- we are migrating from Exchange 2003 to 2010, so both are currently in production. I have a gateway server that drops mail directly to my Exchange 2003 (by IP address), and then mail is scanned by Trend Micro's Worry Free Advanced (v8) and GFI Essentials 2012, and I believe the scan order is Trend first, then GFI. The mail is (then?) delivered to the correct mail server.  I say this with trepidation because I may be unclear on the order.

The problem is this: some outside email from select people never makes it to the users, and don't generate bouncebacks/NDRs. I've done reputation checks on their mail servers and IP's for blacklist/rbl health checks and they are clean. Quarantine search on both Trend and GFI show nothing in the logs, but I can see from my gateway (3rd party) server that the handoff to Exchange on these messages succesfully complete no differently than others.

Users not receiving email aren't specific to one server: some are on Exchange 2010, some on Exchange 2003. I can see it arriving on the 2003 server in the smtpsvc log, and if I go to the message tracker in either server, no results.

I am looking for ideas on identifying the problem, and/or specific log file locations to walk/review.

TIA! Trish
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pbenningfield
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pbenningfield
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EMJSRCommented:
Could it be that the Outlook junk filter has just done its job and your users are simply not checking the Junk Email folder in Outlook? The countless times that has happened to me; if I had a penny...

You also might want to have a look at the TransportAgents in Exchange 2010. That can either be done via the Command Shell or within the Transport Hub tab; maybe Exchange Content Filtering is causing a problem as well.

I had an issue a while back that the Sophos PureMessage AntiSpam transport agent had to be processed before or after (I cannot remember right now) some of the native Exchange transport agent, essentially making some emails not show up for no reason.

This might help you further: http://www.msexchange.org/articles-tutorials/exchange-server-2007/planning-architecture/understanding-transport-agents-part1.html

In the Exchange Management Shell you can type the following command to get a list of all your TransportAgents:

Get-TransportAgent

I hope that provides you with a few pointers.
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pbenningfieldAuthor Commented:
Thanks!  Junk folders wasn't the issue-- adjusting my IMF allowed me to allow email though to the next level of filtering and see what I was losing.
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EMJSRCommented:
Glad I could help!
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