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Exchange 2007 SMTP to Smart Host on SBS server

Looking for some direction.   I'm trying to get Exchange 2007 on a SBS server to forward outgoing mail to Trend Interscan Viruswall 7.0.   and I'm hung up with something in Exchange.    Exchange and ISVW are installed on the same server.    Here's the setup I'm trying to achieve because of that:

Outlook ----->  Exchange SMTP  inbound port 25, out port 26 ----->  ISVW SMTP inbound port 26, outbound port 25 -------> Internet

  Using an Outlook client with a POP3 account setup, I can sucessfully send an e-mail through ISVW on port 26.  However when I try to send an e-mail from the Outlook client through the Exchange account, it gets stuck in Exchange.

  I can see this by using the queue viewer and looking at the queue named "SmartHostConnectorDelivery".  Status on the queue is "retry" and on the mail message it's "Ready".  No Last error is displayed on the e-mail message.

  I configured the Smart Host through the SBS console, network, connectivity.  I also changed the outbound port on the "Windows SBS Internet Send..." connector to port 26.  I did that following the instructions I found in a technet article with the management shell.

So:
A. Should I be using the "SmartHost" feature to do this?
B. Did I modify the right send connector?
C. If so, is there any log or someplece that I can look to see why the mail message is just sitting in that queue?
D. Is there someway to force the queue to try and re-send the message or does it do it automatically every few minutes?

  JimD.

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Jim Dettman (Microsoft MVP/ EE MVE)
Asked:
Jim Dettman (Microsoft MVP/ EE MVE)
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1 Solution
 
shauncroucherCommented:
a) Yes
b) Sounds like it
c) Turn on protocol logging for send and see whats happening: https://exchangepedia.com/blog/2007/05/exchange-server-2007-logging-smtp.html
d) It will retry a few times in a course of minute and then at longer intervals up to 48hrs I believe

Can you run from exchange maangement shell and post:

get-sendconnector | fl Iden*,*port*,*scope*

Shaun
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
<<Can you run from exchange maangement shell and post:

get-sendconnector | fl Iden*,*port*,*scope*>>
Identity                               : Windows SBS Internet Send SRV0
Port                                     : 26
SourceTansportServers : <SRV0>
IsScopedConnector        : False
JimD.
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
BTW, I enabled logging, but nothing shows up in the folder.  Maybe need to stop and start one of the services?
JimD.
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
I stop/started the transport service and verified that logging was set to verbose on the send connector, but still no logging files :(
Nothing is ever simple any more....
JimD.
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
ah...got part of the answer.  Queue on the send connector shows next hop as "srv0.rel.local"  and the queue *does* show a last error:
"451.4.4.0 DS query failed.  The error was: SMTPSEND.DNS.MxLoopback;DNS records for this domain are configure in a loop"
  So apprently, it doesn't like the fact that I'm trying to forward the mail to another SMTP server on the same box.  Not sure how to fix that.
  I'm going to try to specifiy an IP address on the send connector instead of a FQDN.  See if that avoids the MX lookup.
JimD.
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
<<I'm going to try to specifiy an IP address on the send connector instead of a FQDN.  See if that avoids the MX lookup.>>
Smart Host Wizard stops me.  Tells me the IP is invalid because it is the internal address of my Windows SBS server.  
JimD.
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shauncroucherCommented:
Can you post

get-sendconnector | fl

Shaun
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
See attached.
JimD.

[PS] C:\Windows\System32>get-sendconnector | fl


AddressSpaces                : {smtp:*;1}
AuthenticationCredential     :
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
DNSRoutingEnabled            : False
DomainSecureEnabled          : False
Enabled                      : True
ForceHELO                    : False
Fqdn                         : remote.REKELLEY.COM
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : SRV0
Identity                     : Windows SBS Internet Send SRV0
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
LinkedReceiveConnector       :
MaxMessageSize               : 30MB
Name                         : Windows SBS Internet Send SRV0
Port                         : 26
ProtocolLoggingLevel         : Verbose
RequireTLS                   : False
SmartHostAuthMechanism       : None
SmartHosts                   : {srv0.rek.local}
SmartHostsString             : srv0.rek.local
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {SRV0}
UseExternalDNSServersEnabled : False



[PS] C:\Windows\System32>

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shauncroucherCommented:
OK,

Change the fqdn to the local name of the server, or just 'localhost' and try again.

To get the local name go to command prompt and type 'hostname'.

I think the issue is because you are using an external name it is going out then coming back in again, which is confusing matters.

Shaun
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Jim Dettman (Microsoft MVP/ EE MVE)PresidentAuthor Commented:
Bingo!  Thanks a bunch...
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shauncroucherCommented:
Glad I could help

Shaun
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