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Outbound SMTP relay with ISA 2006 - 25.Apr.2007 10:02:32 AM

SKIBUM

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Joined: 25.Apr.2007
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I have read thru the Toms Article on setting up an outbound SMTP relay with ISA server 2004, but it doesn't seem to apply to ISA server 2006. What is the best way to setup ISA 2006 as an outbound SMTP relay agent for exchange 2007?

I would like to use the ISA server to relay outbound email to my hosted Symantec spam filtering service, so that we can filter outbound email thru Symantec. So I guess I would need to configure exchange to send email to the ISA server as a smart host then configure ISA to send email to Symantec as a smart host.

Any help would be greatly appreciated.

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RE: Outbound SMTP relay with ISA 2006 - 26.Apr.2007 2:01:42 PM

tshinder

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From: Texas
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Works the same with ISA 2006 as ISA 2004 Firewalls. Only difference is that there is NO SMTP message screener for 2006 Firewalls.

As for Exchange 2007 requirements, I don't know. I'm boycotting it until they come up with a functional user interface.

HTH,
Tom

_____________________________

Thomas W Shinder, M.D.
Sr. Consultant/Technical Writer
Prowess Consulting http://www.prowessconsulting.com/
Blog: http://blogs.isaserver.org/shinder/

GET THE NEW ISA 2006 Book!: http://tinyurl.com/2gpoo8

(in reply to SKIBUM)

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RE: Outbound SMTP relay with ISA 2006 - 17.Apr.2008 3:48:08 PM

mmayou

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Joined: 17.Apr.2008
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Hi, Skibum

I was wondering if you ever found a good answer, as I have a similar problem with an Exchange 2003, ISA2006 setup. My filtering is done by MXlogic whom I have as a smarthost. I can replace them with the ISA, but can see nowhere in the configuration to have the ISA send only to MXlogic. Did you get it resloved?

Thanks, Mike

(in reply to SKIBUM)

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RE: Outbound SMTP relay with ISA 2006 - 21.Apr.2008 9:49:59 AM

Christoph37

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Joined: 13.Mar.2006
Status: offline

Hi, Mike,

define a new computer set and add to it the IP addresses of MXlogic�s SMTP servers.

Then you can set up a rule, in which you allow Outbound SMTP traffic from your mailservers to the new computerset.

On the Exchange server, if not already done, create an SMTP connector that sends mail to the SMTP server(s) of MXlogic. If you enter IP addresses for the smart host, you will have to enclose them in square brackets ([<ip.address>])

HTH

Christoph

< Message edited by Christoph37 -- 21.Apr.2008 9:54:18 AM >

(in reply to mmayou)

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RE: Outbound SMTP relay with ISA 2006 - 22.Apr.2008 1:06:28 PM

tshinder

Posts: 47490
Joined: 10.Jan.2001
From: Texas
Status: offline

Hi Christoph,

Very good answer!

Thanks!
Tom

_____________________________

Thomas W Shinder, M.D.
Sr. Consultant/Technical Writer
Prowess Consulting http://www.prowessconsulting.com/
Blog: http://blogs.isaserver.org/shinder/

GET THE NEW ISA 2006 Book!: http://tinyurl.com/2gpoo8

(in reply to Christoph37)

Post #: 5

RE: Outbound SMTP relay with ISA 2006 - 14.May2008 11:11:17 AM

bhavin78

Posts: 429
Joined: 18.Jul.2005
From: USA
Status: offline

My outbound email is not working when publishing exchange server on ISA 2006 (ISA is not a domain member)
I tried to manually send email from Exchange server and here is the result.
telnet gsmtp147.google.com 25
Connecting To gsmtp147.google.com...
Could not open connection to the host, on port 25: Connect failed
Logs on Firewall says SMTP connection on port 25 initiated.

I have allowed outbound smtp from internal to Ext

(in reply to Christoph37)

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RE: Outbound SMTP relay with ISA 2006 - 14.May2008 12:42:03 PM

tshinder

Posts: 47490
Joined: 10.Jan.2001
From: Texas
Status: offline

That mail server doesn't allow telnet connections. I can telnet to other mail servers.

HTH,
Tom

_____________________________

Thomas W Shinder, M.D.
Sr. Consultant/Technical Writer
Prowess Consulting http://www.prowessconsulting.com/
Blog: http://blogs.isaserver.org/shinder/

GET THE NEW ISA 2006 Book!: http://tinyurl.com/2gpoo8

(in reply to bhavin78)

Post #: 7

RE: Outbound SMTP relay with ISA 2006 - 14.May2008 1:41:43 PM

bhavin78

Posts: 429
Joined: 18.Jul.2005
From: USA
Status: offline

how can I fix the outbound smtp issue, any time I send email it sit's in the queue.

I tried to send manual email from exchange and here is the error
telnet smtp.att.yahoo.com 25
elho yahoo.com
220 smtp119.sbc.mail.re3.yahoo.com ESMTP
ehlo yahoo.com
250-smtp119.sbc.mail.re3.yahoo.com
250-AUTH LOGIN PLAIN XYMCOOKIE
250-PIPELINING
250 8BITMIME
mail from:bhavin78@bhavin.us
530 authentication required - for help go to http://help.yahoo.com/help/us/sbc/d
sl/mail/pop/pop-11.html

(in reply to tshinder)

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RE: Outbound SMTP relay with ISA 2006 - 15.May2008 6:13:01 AM

tshinder

Posts: 47490
Joined: 10.Jan.2001
From: Texas
Status: offline

It looks like authentication is required.

HTH,
Tom

_____________________________

Thomas W Shinder, M.D.
Sr. Consultant/Technical Writer
Prowess Consulting http://www.prowessconsulting.com/
Blog: http://blogs.isaserver.org/shinder/

GET THE NEW ISA 2006 Book!: http://tinyurl.com/2gpoo8

(in reply to bhavin78)

Post #: 9

RE: Outbound SMTP relay with ISA 2006 - 15.May2008 10:27:11 AM

bhavin78

Posts: 429
Joined: 18.Jul.2005
From: USA
Status: offline

do I have to configure smart host on SMTP with authentication ?

Is it trying to use smtp.att.yahoo.com as my SMTP server? I have DSL service from AT&T .

or May be SMTP port is not open for me, if thats' the case, what are my options?

< Message edited by bhavin78 -- 15.May2008 4:14:13 PM >

(in reply to bhavin78)

Post #: 10

RE: Outbound SMTP relay with ISA 2006 - 16.May2008 11:33:02 PM

bhavin78

Posts: 429
Joined: 18.Jul.2005
From: USA
Status: offline

I got my outbound SMTP to work. Port 25 was blocked by At&t, they opened the port and my outbound email started working.

I still cannot send email to hotmail as they dont accept email from server with dynamic IP . I am not also able to send email to my yahoo.

Is there any workaround for making email to hotmail and yahoo account work?

Is there any free SPAM filtering service I can use on my test exchange server?

Thanks for all your help

(in reply to bhavin78)

Post #: 11

RE: Outbound SMTP relay with ISA 2006 - 18.May2008 12:08:46 PM

tshinder

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Joined: 10.Jan.2001
From: Texas
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quote:

ORIGINAL: bhavin78

do I have to configure smart host on SMTP with authentication ?

Is it trying to use smtp.att.yahoo.com as my SMTP server? I have DSL service from AT&T .

or May be SMTP port is not open for me, if thats' the case, what are my options?

If you're going to use a Smart Host, you have to make sure that the provider intends on providing that feature. You need to ask your ISP if they provide Smart Host capabilities to their customers, if so, it's only going to be for their corporate account customers. However, if they give you an email account, you might be able to use the settings that you use for your email client application.

HTH,
Tom

_____________________________

Thomas W Shinder, M.D.
Sr. Consultant/Technical Writer
Prowess Consulting http://www.prowessconsulting.com/
Blog: http://blogs.isaserver.org/shinder/

GET THE NEW ISA 2006 Book!: http://tinyurl.com/2gpoo8

(in reply to bhavin78)

Post #: 12

RE: Outbound SMTP relay with ISA 2006 - 18.May2008 12:11:20 PM

tshinder

Posts: 47490
Joined: 10.Jan.2001
From: Texas
Status: offline

quote:

ORIGINAL: bhavin78

I got my outbound SMTP to work. Port 25 was blocked by At&t, they opened the port and my outbound email started working.

I still cannot send email to hotmail as they dont accept email from server with dynamic IP . I am not also able to send email to my yahoo.

Is there any workaround for making email to hotmail and yahoo account work?

Is there any free SPAM filtering service I can use on my test exchange server?

Thanks for all your help

There are places that do store and forward for email, like TZO. The service is designed to get around the problem that small biz has with hosting their own email and getting whacked as spam because the address reverse lookup shows it to be dynamic.

Tom

_____________________________

Thomas W Shinder, M.D.
Sr. Consultant/Technical Writer
Prowess Consulting http://www.prowessconsulting.com/
Blog: http://blogs.isaserver.org/shinder/

GET THE NEW ISA 2006 Book!: http://tinyurl.com/2gpoo8

(in reply to bhavin78)

Post #: 13