Enable verbose logging on the send-connector and look at the actual SMTP stream 
being sent to SurfControl.

From: [email protected] [mailto:[email protected]] On 
Behalf Of Robert Cato
Sent: Tuesday, August 6, 2013 11:21 PM
To: [email protected]
Subject: [Exchange] Message Routing


Environment: Exchange 2007 with all SPs and updates installed
Websense SurfControl in the DMZ as the smarthost/edge server

Problem: Most outbound mail is not affected. All emails to certain domains are 
getting hung in the SurfControl queues.
Using mxtoolbox.com<http://mxtoolbox.com>. Our domain is not on any blacklists 
and the DNS information is correct. The SMTP test checks out good with some 
warnings on connection time and transaction time. I ran the 
mxtoolbox.com<http://mxtoolbox.com> tests against a couple of domains we know 
we can't deliver to and they check out clean. I sent a message from my gmail 
account to one of the domains and it got there immediately.
We have a spf record.
The reject messages are being generated by SurfControl and are not helpful:

Your message could not be sent to all recipients yet. The system will keep 
retrying.

**THIS IS A WARNING ONLY. YOU DO NOT NEED TO RESEND YOUR MESSAGE **

Details:

    Failed to send to: [email protected]<mailto:[email protected]>

    Failed attempts: 12

    Last attempt: Tue, 06 Aug 2013 13:50:16 -0400

    Status: [email protected]<mailto:[email protected]>: 
[cust31236-4.in.mailcontrol.com<http://cust31236-4.in.mailcontrol.com>], 
Incomplete SMTP session (cause: idle timeout 
[cust31236-4.in.mailcontrol.com<http://cust31236-4.in.mailcontrol.com>]).
We have checked blacklists on several sites. The test on 
blacklistcheck.com<http://blacklistcheck.com> did pop positive for 
fl.chickenboner.biz<http://fl.chickenboner.biz>, but I am not finding much 
helpful about getting off their list.

The SurfControl server is managed by another team, and they said that more 
verbose logs were not available. (I find that hard to believe)

Any ideas for troubleshooting or resolution are greatly appreciated.

Robert

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