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Mail will not send from one internal site to another

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Mail will not send from one internal site to another - 27.Sep.2014 11:58:32 AM   


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Joined: 27.Sep.2014
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Ok, we have a really odd issue. We have one single site which will not route mail to another single internal site. Messages between the site and another internal site flow normally.

Our set-up is as follows:
Site 1 - Exchange 2007 & Exchange 2003 servers
Site 2 - Exchange 2007 server
Site 3 - Exchange 2003 Server
Site 4 - Exchange 2007 server

All sites are connected to the other three sites using VPNs in a mesh configuration.

Site 1 can send and receive with Site 2
Site 1 can send and receive with Site 3 (site 1 holds the 2007<->2003 RGC)
Site 2 can send and receive with Site 4
Site 3 can send and receive with Site 2 (via Site 1)
Site 1 can SEND to Site 4
Site 4 is having problems sending to Site 1 (and Site 3 as 2003 traffic goes through Site 1)

Also, as Site 4 is on a dynamic IP address it use Site 1 as a SmartHost for external mail and this is also having problems.

Some messages from Site 4 do get through to Site 1 but it seems a bit random. Almost all messages with attachments do not get through, most messages without attachments do get through but not all. It does not seem to be related to the size of the message as a 15Kb message with no attachment was delivered but a message with a 1kb text file attached is stuck in the queue.

I have checked the SMTP send and receive logs and it all seems to stop at the BDAT command - after this the next log entry for the message comes after the timeout period and is one of the following errors:

SMTP Receive logs
421 4.4.1 Connection timed out
451 4.7.0 Timeout waiting for client input

SMTP Send logs
421 4.4.1 Connection timed out
412 4.4.2 Connection dropped
Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time or established connection failed because connected host as failed to respond <ip address of Site 1 2007 server)

Originally Site 1 used the same receive connector for both Site 2 and Site 4 - I have since created a specific one for Site 4 to allow me to more easily monitor the logs and to alter settings without affecting Site 2.

I have Googled extensively on these error messages and have set the receive connectors as advised on several sites:
General tab - checked the FQDN is correct, max message size set to 100Mb
Network tab - Local set to IP address of the server, Receive mail from set to the IP addresses of all the other Exchange servers
Authentication tab - all boxes checked except Externally Secured
Permission Groups tab - all boxes checked except Partners

As I said above, with these settings mail from Site 2 is received with no problems, if I change the settings it does affect the flow from Site 2 which is why I have moved Site 4 to it's own receive connector.

I have used MS Network Monitor and it looks like the SMTP conversation seems to stop after the BDAT command but this could be down to my lack of knowledge with the Network Montior software.

I have tried various suggestions:

Disabled BinaryMime and Chunking - SMTP log showed it stopped after 354 Start mail input prompt then acted the same as before.

Checked firewalls between the sites - no SMTP filtering in place, Site 1 and Site 2 have the same make of firewall and the settings are the same.

Checked message size limits on the Send Connectors including the hidden Intra-Org send connectors - all set to Unlimited

Changed the timeout on the receive connector - this just delays the error responses shown above.

I am totally at a loss here - if there were no messages going through it would make things easier as there would be a definite issue to identify, but as some get through and some don't and the fact that it is only the messages between two of the three Exchange 2007 servers makes it trickier to find.

The only other thing I can think of is something to do with versions compatibility and that I have missed a setting that only applies between certain OS and Exchange versions.

Site 1 is Windows 2008 R2 x64 and Exchange version 8.3 (Build 83.6)
Site 2 is Windows 2008 R2 x64 and Exchange version 8.1 (Build 240.6)
Site 4 is Windows 2008 x86 and Exchange version 8.1 (Build 240.6)

I know the configuration of Site 4 is not ideal, but it has been working fine until we had a big AD issue which involved demoting some DCs and in some cases having to do a /forceremoval due to problems synchronising between the sites. Site 4 holds a DC as well as the Exchange server which I know is not recommended but at the time I only had sufficient budget for one server in Site 4. It did allow me to promote it back as a DC after the /forceremoval which I have since been told that it should not have done - could this be the source of the problems?

If there is anything else anyone can suggest I would be most grateful - I have tried just about every suggestion that I can find by Googling the error messages, 'Exchange 2007 SMTP problems', "Exchange 2007 Receive Connector problems', etc.

Many thanks, Eddie
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