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iis smtp nntp : SMTP not sending email to domain that matches servername


MarkSJ
2/27/2006 4:36:27 PM
I have a 2003 Web Edition Server that acts as a SMTP email server using IIS.
It has one domain setup on it (domain.local), setup on our internal network
behind a firewall. All email goes out ok. There is a MX record for
domain.com that points at a hosting company. This is where we pick up our
incoming mail.
I have a problem where we suffer from emails being rejected due to reverse
DNS lookups. I'm guessing (and I hope someone can confirm this) I need to
move the smtp server to the DMZ, make available an external IP for this
server, and change the servername from domain.local to something like
smtp.domain.com.
Now if I change the domain on the server to domain.com - all emails sent out
via that server that need to go to user@domain.com won't actually get sent
out. They end up residing locally.
My question is how do I get the emails sent to users@domain.com to go out
when the servername is called domain.com.
Also any suggestions on how to solve the reverse DNS lookup would be most
Sanford Whiteman
2/28/2006 12:25:18 AM
[quoted text, click to view]

I feel like I'm writing on this a lot lately. :)

You do not need to change the Windows name of this machine. However,
you do need to create a public IP dedicated to this machine; that may
mean putting the machine in a non-NATted DMZ, or adding a static NAT
for it, depending on your firewall. The PTR for that IP address
_must_ complete an EHLO-PTR-A-IP "DNS roundtrip" to ensure delivery.
That is, the PTR for that IP must match the EHLO sent by that IP, and
the PTR must also have a corresponding A record that points back to
the originating IP.

IIS SMTP uses the FQDN setting under Delivery-Advanced as the EHLO for
the virtual server. By default, this is set to the Windows name of
the machine. Changing it overrides the relationship to the Windows
name, so you don't need to change anything outside of IIS.

[quoted text, click to view]

The VS FQDN should certainly _not_ be domain.com. The PTR record,
which should be the same as the VS FQDN -- as I mention above, reused
by IIS as the EHLO -- should be the canonical name assigned to the
machine. The canonical name of the machine may be thought of as the
"actual" or "real" unique hostname of the machine and must be a
fully-qualified hostname resolvable using public DNS. It should
therefore be something along the lines of smtp.domain.com. The
virtual server's local drop directory would thus only grab messages to
user@smtp.domain.com.

Also look at recent n/g posts from me on this exact topic.

MarkSJ
3/5/2006 3:14:27 PM
Ok, I have sorted out the email server no problem and also the external IP.
I can create the A record but for some reason I don't have the option of
creating the PTR record. I'm assuming I should have an option to create a
PTR record on the same DNS server in charge of the domain. The only options
I have are MX, CNAME, NS and A. Does the PTR have to be done by the ISP? Any
ideas?

Thanks for your comments below by the way ... most useful.

[quoted text, click to view]
Sanford Whiteman
3/5/2006 11:28:12 PM
[quoted text, click to view]

Unless it has been delegated to you, yes, and this is usually at the
customer's deliberate request. What is the IP address in question? I
can tell you what the nameservers are for the reverse domain.

[quoted text, click to view]

Glad to hear it.

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