Exchange 2003 Not sending to ISP's SMTP Server

From: Steve (anonymous_at_discussions.microsoft.com)
Date: 02/16/04 

Date: Sun, 15 Feb 2004 17:26:36 -0800

When using your ISP's SMTP server as a smart host, I have
found that some ISP's use filters to read the senders
email address and block all mail that is not not coming
from the ISP's mail addresses.

For example I can send mail through RoadRunners SMTP
servers using our domain name in the sender address, but I
cannot do that with QWEST SMTP servers.

Could this be a possibility in your case ?

>-----Original Message-----
>Hello,
>
>This might be a bit long winded but I want to paint as
>complete a picture as possible of my problem.
>
>I have installed Microsoft Small Business Server 2003
>including Exchange Server 2003.
>
>The Server is a local domain and is not out on the
>internet. It is server.home.local.
>
>We are using POP connectors for e-mail that are used with
>our ISP. They are not hotmail, or yahoo mail and stuff
>like that. They are mail accounts set up by the same ISP
>we use for Internet Access. Its mail server for both
>POP and SMTP are mail.ptdprolog.net.
>
>We have one single NIC card in the server. This is
>connected to a 16 Port 3COM hub. The internet is
>connected through our local CABLE Internet provider.
>(Prolog) The cable modem is connected to a Linksys
>Cable/DSL router which uses NAT translation, which is
>then connected to the 3COM hub.
>
>On a side note, users who have used Outlook Express on
>the same network are able to send and receive e-mail
>without any problems, so I know the information is
>passing through the router just fine On port 110 and port
>25.
>
>We are now taking these users who used Outlook Express
>and who checked their e-mail through their own Outlook
>Express and moving them to Outlook and using an Exchange
>Server to check on their POP accounts in place of each of
>the users using getting their e-mail separately.
>
>I ran the wizard that comes with SBS2003 and configured
>all of the POP accounts correctly, and when it came time
>to configure the SMTP host, I choose to use my ISP's SMTP
>mail server which is mail.ptdprolog.net.
>
>Exchange will now go out and receive all of the POP3 e-
>mail without a problem. I see it building up in the
>users Mailboxes each time it checks e-mail. So I know
>that is working.
>
>But when a user tries to send e-mail through our ISP's
>SMTP host it never makes it. Most of the time we receive
>a bounce back telling us that the SMTP server
>(server.home.local) was rejected. OF course this is the
>inside host and not the mail.ptdprolog.net where it
>supposed to go.
>
>I have gone into Exchange Management, and made sure it
>created a smart host for the outside SMTP, which is did.
>But it continues to route it to the incorrect host.
>
>I then went into the Virtual SMTP Host setting and
>noticed that it did have server.home.local in one of the
>setting, but right under this setting it had SMARTHOST
>and it was set to mail.ptdprolog.net.
>
>However, it's still not functioning correctly. My ISP
>does not block PORT 25 sends at all. There is no login
>requirements with the exception that you must be using
>their domain to send e-mail, or you must be a user
>connected to their system to send which I am.
>
>Outlook Express sends e-mail without problems. On
>another side note, does anyone know how Outlook Express
>sends e-mail? (IE: ETURN or other)
>
>I have tried changing setting on the way it connects with
>the SMTP server but none of them work. I have gone into
>the SMTP Virtual Server and changed the one setting of
>server.home.local to mail.ptdprolog.net and had no
>effect. Of course everything has been returned to its
>original settings until I figure this one out.
>
>At this point, I'm stumped. I have not really made any
>changes to the default setting that were made when I ran
>the INTERNET wizard in the TO DO list of SBS2003. In
>SBS2000, this works flawlessly. And pertaining to the
>POP connectors, it did set them up correctly, but it
>refuses to send any e-mail to my ISP's SMTP host.
>
>My ways of testing this are using OWA as the
>administrator, and sending it to an outside account which
>I can check through the web also. I will send an e-mail
>and then check the cue line to see if it's held up. It
>is. Sometimes it will bounce right away. Others take a
>while longer. But the e-mail never makes it to my ISP
>because when I check that account, it never shows the e-
>mail.
>
>I am not getting any errors in the Event Viewer. SO I
>really don't have much in the way or reporting errors
>back.
>
>HELP!
>
>I have never had this problem before, and after scouring
>these newsgroups for days, It seems it might possible
>that I might be the first to have this problem. What am
>I doing wrong?
>
>Is there an internal setting I need to change?!?!?! Is
>there a way of testing this in other ways other then the
>way I'm testing it now?!??!
>
>Thanks for all your help, and reading my long winded plea
>for help
>
>Take Care, Tom
>
>.
>

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