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ohioholiday

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sbs 2003 R2 - ISA blocking internal SMTP relay

Trying to allow our Contract Manager server to "relay" to our Exchange 2003 SBS 03R2 server.

Somehow the ISA 2006 keeps stopping it.  It never gets to the SMTP.

Things I have done:
I allowed the IP of the server as a relay in SMTP VIrtual properties
I added a firewall rule allowing mail protocols from contract manager server to internal/external/local

Doesn't seem to matter.  Keep getting 2 logs in ISA monitor:
1.  When email is sent from contract manager, this appears:
Initiated Connection
SERVERNAME 9/20/2011 3:53:48 PM
Log type: Firewall service
Status: The operation completed successfully.
Rule: CM Email
Source: Internal ( 192.168.xxx.xxx:4559) Destination: Local Host ( 192.168.xxx.xxx:25) Protocol: SMTP

2.  Then the handshake is dropped with this error:
Closed Connection
SERVERNAME 9/20/2011 3:54:48 PM
Log type: Firewall service
Status: A connection was gracefully closed in an orderly shutdown process with a three-way FIN-initiated handshake.
Rule: CM Email
Source: Internal ( 192.168.100.4:4559) Destination: Local Host ( 192.168.100.9:25) Protocol: SMTP

Full error message in isa monitoring log shows:  0x80074e20 fwx_e_graceful_shutdown

So it seems to me that this is definitely being blocked by ISA.  Contract Manager requires anonymous authentication for SMTP relay - so maybe I should setup a separate smtp outbound for this email relay?

THoughts/steps/recommendations?
Avatar of Keith Alabaster
Keith Alabaster
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If ISA was blocking then ypou would receive a denied message in the log - the messages you are reporting above are clean, 'completed' messages against the traffic ISA has been asked to pass. I would go back to the Exchange arena and check there again first as it looks like ISA does not get sight of the full transaction.
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ohioholiday

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