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Outbound mail from Small Business Server 2003

Posted on 2008-11-04
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I need some help configuring outbound mail from SBS2003

Although I have configured a few servers using the CEIC Wizard, that is not working in this case.  Neither the ISPs smtp server, nor DNS are working from the standard SBS configutration GUI.  I suspect that the ISP is blocking the outbound traffic, but I don't have the necessary skills to know how to confirm this.  I can offer the following information:

Outbound mail from Outlook on a stand alone PC works at this site with the ISP's smtp server (mail.bellsouth.net) and no authentication is needed

Outbound mail from SBS2003 does not work at this site with the ISP's smtp server (mail.bellsouth.net)

Outbound mail from Outlook on a stand alone PC at this site works with a smarthost at GoDaddy when the outbound SMTP prort is set to 80 and authentication is configured (smtpout.secureserver.net)

Outbound mail from SBS2003 does not work with a smarthost at GoDaddy -- I don't now how to setup authentication in SBS for this account, or change the outbound smtp port.

I have looked at the configuration of the SMTP connector in Exchange  (both SBS mangement "advanced" options, as well as MS Exchange System Mgr., but several "guesswork" solutions have failed to to get any mail flowing out of this server

Inbound mail via the default POP3 connector in SBS2003 is working fine.
No firewall on my side other than NAT on a linksys router
ISP is bellsouth.net residential service
Static IP at this site

Much thanks in advance for any help with this.

Peter Tiemann
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Question by:pntiemann
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LVL 5

Expert Comment

by:buddhole
ID: 22880987
Does the bellsouth smtp server requires authentication ? If so, you can setup an exchange connector to use the bellsouth server as a smart host with authentication. Scroll down on this page to check the settings: http://www.christensen-software.com/support/config_exchange_2003.htm
 
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Author Comment

by:pntiemann
ID: 22881971
Thanks for posting.

When I configure an Outlook POP account, no authentication is required for the bellsouth smtp server.  I'll check your link...
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Expert Comment

by:buddhole
ID: 22882045
Rereading your question I think the problem might be more related to SBS than to traffic filtering. If port 25 is blocked by the ISP, Outlook shouldn't be able to send mail. Test the traffic with telnet from the sbs server. Type "telnet smtp.xs4all.nl 25" and see if you get an answer. (xs4all is a dutch ISP).
As you stated, the wizards don't work, maybe try SBS 2003 Best Practices Analyser. Also check if ISA 2004 is installed and configured correctly. BPA is available at  http://www.microsoft.com/downloads/details.aspx?familyid=3874527A-DE19-49BB-800F-352F3B6F2922&displaylang=en
 
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Author Comment

by:pntiemann
ID: 22883279
No luck with telnet on Port 25, to your suggested FQDN, or another one I have used, but...

When I try to connect via telnet to a smarthost at my mail hosting provider, I have success.  The smart host accepts the connection on port 80.  This is by design, i assume because of anti relaying issues on port 25 at some ISPs

I guess I need tofigure out how to configure SBS to send to the smarthost on Port 80

Will check out the BPA link... Thanks!

FYI, Christen-software link was informative, but I think I already tried the procedures outlined there.  I'll look at it again to be sure.

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Accepted Solution

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buddhole earned 750 total points
ID: 22884039
You can set the outgoing port per smtp virtual server:
SMTP virtual server -> Properties --> Delivery Tab --> Outbound Connections --> TCP Port.
There you can set it to 80.
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Author Comment

by:pntiemann
ID: 22884859
What about setting authentication (username/password) for the smarthost connection?

Also, in response to your previous comment, IA'm not using ISA server on the SBS Box.

Thks.
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Author Comment

by:pntiemann
ID: 22885286
update -

I changed the otbound port - I had to use Exchange System Mgr>Servers>myserver>Protocols>SMTP>Default SMTP Virtual Server>Properties>Delivery Tab>Outbound Connections Button>TCP Port Value

Now when I go to SBS System manager console the Queue for myserver  SmallBusiness SMTP connector - smtpout.secureserver.net has cleared, but no mail is being delivered to the receipient

Instead, my Outlook client gets an NDR with the folowing msg.:

Your message did not reach some or all of the intended recipients.

      Subject:      test1
      Sent:      11/5/2008 6:55 AM

The following recipient(s) cannot be reached:

      ptiemann@yahoo.com on 11/5/2008 6:55 AM
            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <dts-nola.com #5.5.0 smtp;553 Sorry, that domain isn't in my list of allowed rcpthosts.>

Sorry this is so complicated....

Any advice is appreciated.  My gut feeling is to just look to find a different ISP, as I'm guessing that that is the issue.  Still, you'd like to think there's a way to make this work.

PNT
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Author Comment

by:pntiemann
ID: 22886997
... or definitvely identify the source of the problem.
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Assisted Solution

by:Press2Esc
Press2Esc earned 750 total points
ID: 22887466
bellsouth, aswith all majot isp's, block port 25 for residential accounts...  if the client wants to use their own domain.mail server, they will need to upgrade to business-class. bellsouth/at&t business dsl do not block port 25.  also, smarthosting & mail relay on the residential account will not work.
in any case, you will need a valid rDNS/PTR record for the sbs mail server, as many of the major isps perform a reverse lookup any incoming mail..
P2E
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Author Comment

by:pntiemann
ID: 22889099
10-4, and thanks to both off you.

PNT
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LVL 5

Expert Comment

by:buddhole
ID: 22889116
Press2Esc has some good tips there. I was referring to the exchange system manager setings, not ISA. Apologies for the confusion.
Reading your last post you are using a connector (smtp.secureserver.net) and a smart host (mail.bellsouth.com) ? I'ld suggest removing the connector and only use mail.bellsouth.net as smart host in the SMTP virtual server settings.
Googling I found this link with info on someone who got exchange working on a residential connecction from bellsouth: "The key is to list mail.bellsouth.net as the smarthost but do NOT authenticate the connection. I also gave my FQDN...the long ADSL-----sip.asm.bellsouth.net as the response to EHLO but don't know if that matters.
http://www.dslreports.com/forum/r19372023-Home-Network-Bellsouth-Smarthost-and-Exchange-Server.
 
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Expert Comment

by:buddhole
ID: 22889137
Again, remove the secureserver.net connector and try it with the smart host and the suggestions. Maybe you'll get it working at last. Thanks for the points.
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Author Comment

by:pntiemann
ID: 22897038
buddhole -
Thanks for the extra effort.  Wish I could award some more points.  I'll try your suggestions, and post back the results.

PNT
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LVL 5

Expert Comment

by:buddhole
ID: 22899636
Don't worry, you already gave me points. Hopefully it helps.
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