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SMTP Server failed connection attempt

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SMTP Server failed connection attempt - 4.Sep.2008 12:19:21 PM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
I have a new ISA 2006 server that is intended to replace an ISA 2004 server.

I have an Exchange publishing rule on the 2006 server that is identical to the 2004 rule.  When I set my smarthost in the DMZ (on Watchguard) to forward incoming mail to the external port of the 2006 server, I see an error of:

10.1.0.200    ISA01 -  TCP -    No  -    9/4/2008 3:40:06 PM 2020 21047 0 0 0x8007274c WSAETIMEDOUT  0x0 0x0 Firewall - 9/4/2008 10:40:06 AM 172.16.0.16 25 SMTP Server Failed Connection Attempt Mail - Incoming SMTP Server 10.1.0.200  External Internal - 

It is the same smarthost, but it can't send through the ISA 2006 server.  Any ideas?
Post #: 1
RE: SMTP Server failed connection attempt - 4.Sep.2008 1:19:34 PM   
IanC

 

Posts: 338
Joined: 11.Jul.2007
From: UK
Status: offline
Hi,

A possible explaination could be that the internal mail server's default gateway is still pointing (either directly ot indirectly) to the ISA 2004 server.  If so, you can fix the problem by either changing the DG or amending the publishing rule so that Requests appear to come from the ISA Server computer.
 
Ian

_____________________________

Ian Currie

nAppliance TMG/UAG Appliances - EMEA
www.surefront.co.uk

(in reply to tjcarst)
Post #: 2
RE: SMTP Server failed connection attempt - 4.Sep.2008 2:09:47 PM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
Thanks, IanC.  I had changed the default gateway on the Exchange server to point to the new server.  The error was still there.  I can try again and see if it is still logging the error.

(in reply to IanC)
Post #: 3
RE: SMTP Server failed connection attempt - 4.Sep.2008 2:23:39 PM   
paulo.oliveira

 

Posts: 3472
Joined: 3.Jan.2008
From: Amazon, Brazil
Status: offline
Hi,

were you using the message screener with ISA 2004?

Regards,
Paulo Oliveira.

(in reply to tjcarst)
Post #: 4
RE: SMTP Server failed connection attempt - 4.Sep.2008 2:24:28 PM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
No, I was not using the Message Screener.

(in reply to paulo.oliveira)
Post #: 5
RE: SMTP Server failed connection attempt - 4.Sep.2008 3:05:57 PM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
After re-attempting the change, I see this error (it appeared before as well).

There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
          <exc03.madonna.org #5.5.0 smtp;553 The sender is spoofed.>

All that has changed:
All rules on incoming firewall changed to point to external ISA 2006
Gateway on Exchange set to internal port of ISA 2006
SMTP Delivery on Smarthost in DMZ set to external ISA 2006

I can't find anything else to change.  The Internet Mail connector on Exchange still points to the smarthost in the DMZ - nothing changed here.

< Message edited by tjcarst -- 4.Sep.2008 3:23:59 PM >

(in reply to tjcarst)
Post #: 6
RE: SMTP Server failed connection attempt - 4.Sep.2008 3:41:31 PM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
As soon as I set the default gateway on Exchange back to ISA 2004, messages are delivered to outside domains without the Spoof error.

(in reply to tjcarst)
Post #: 7
RE: SMTP Server failed connection attempt - 5.Sep.2008 10:52:55 AM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
quote:

ORIGINAL: IanC

Hi,

A possible explaination could be that the internal mail server's default gateway is still pointing (either directly ot indirectly) to the ISA 2004 server.  If so, you can fix the problem by either changing the DG or amending the publishing rule so that Requests appear to come from the ISA Server computer.
 
Ian


The incoming SMTP rule is published, but the outside is not a publishing rule.  Changing the incoming rule so Requests appear to come from the ISA Server computer did not work.  Same error.  553 the sender is spoofed.

(in reply to IanC)
Post #: 8
RE: SMTP Server failed connection attempt - 5.Sep.2008 11:41:55 AM   
tjcarst

 

Posts: 184
Joined: 6.May2004
From: Lincoln, NE
Status: offline
Thanks for the responses.  The problem was the smarthost in the DMZ.  The new external IP of ISA was added, but a restart was needed.  All seems fine now.

(in reply to tjcarst)
Post #: 9

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