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ISA server with multiple IP addresses, only one visible

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ISA server with multiple IP addresses, only one visible - 26.Jul.2010 11:18:51 PM   
bigapple99

 

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Joined: 26.Jul.2010
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Hi All

I have an ISA 2006 on running on a Windows 2003 box with multiple public address assigned to the external NIC, ranging from 120.x.x.2 to 120.x.x.5. The internal network uses NAT and running Exchange 2007 on one of servers(windows 2008). I set up the MX record point to 120.x.x.3 and create SMTP server publishing rule on ISA.
The problme arise when some email servers block me due to lack of a reverse DNS record. Icheck out the error message and find out they believe the emails are sent from 120.x.x.2, not  120.x.x.3. I realized even if I have multiple public IP addresses on the ISA, I can't choose which IP address Exchange to use to send out emails to internet.
Anyone has a solution? General speaking, why hosts on the internet can only see 120.x.x.2? How can I make other IP visible when SENDING OUT something?

Thanks
Post #: 1
RE: ISA server with multiple IP addresses, only one vis... - 28.Jul.2010 3:52:55 AM   
Jason Jones

 

Posts: 4663
Joined: 30.Jul.2002
From: United Kingdom
Status: offline
This is expected behaviour and a well known ISA issue.

This is the best you can do without an upgrade to TMG:

http://www.collectivesoftware.com/Products/IPbinder

Alternatively, change your MX record to use .2 and publish SMTP on .2

Cheers

JJ

_____________________________

Jason Jones | Forefront MVP | Silversands Ltd
My Blogs: http://blog.msedge.org.uk/ and http://blog.msfirewall.org.uk/

(in reply to bigapple99)
Post #: 2
RE: ISA server with multiple IP addresses, only one vis... - 22.Jul.2011 4:05:48 PM   
manning

 

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Joined: 9.Oct.2006
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Sorry to drum up and hijack this old thread, but it relates to what I am getting ready to do. Let's assume TMG is not a budget option.

So, the failures the OP saw were due to mismatch in sending IP of the ISA server versus the IP for the MX record. I am currently upgrading to a new Exchange server from Exchange 03 to 07. The old Exchange 03 server sends and receives through an oooold ISA 2000 box with addresses from a /29 subnet. I am about to change my MX record to a /25 subnet so when I finish moving the traffic over to our ISA 2006 box we have many more IPs available to use for web publishing and such, but want to make sure I don't assign it an address that will run into same issue. 

Anyway, I just want to make sure I understand, for smtp to work without the mismatch issue, you have to make sure the first IP bound to the external NIC is the same as the MX record in the public DNS? As long as that is the case, all is good?

And while I'm at it, OWA's listener and a Barracuda Spam appliance server publishing rule and such can (must) all use that same IP without any issue, correct?

< Message edited by manning -- 26.Jul.2011 3:39:23 PM >


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Manning

I only do this because I have to.

ISA 2006 standard on Server 2k3 R2

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RE: ISA server with multiple IP addresses, only one vis... - 25.Oct.2011 11:38:48 PM   
zaralansss

 

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RE: ISA server with multiple IP addresses, only one vis... - 6.Dec.2011 12:58:03 PM   
pwindell

 

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Joined: 12.Apr.2004
From: Taylorville, IL
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It doesn't really have anything to do with the MX Record itself.  In fact the MX Record points to another Host Record, not an IP#.

What you need is for the IP# the outbound mail is tagged with to Reverse Resolve to the right Domain Name.

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Phillip Windell

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