Configure new integral Windows 2008 R2 SMTP service

aPendLtd
aPendLtd used Ask the Experts™
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Hello,
I'm using Windows Server 2008 R2 with the integral SMTP service on port 125.
This server is a Web Server that contains two websites: aaa.com and aaa.net (for example), these websites are sending emails through this service.

In addition, I have hMailServer installed on the server - hMail is using ports 25 (SMTP) and 101 (POP3) - this mail server is used for the Info \ Sales \ NoReply and some other mailboxes.

I'm using TMG FW and ports 110 \ 25 \ 80 \ 443 are opened from the world to my server.

Two big issues:
1. I need to configure the pointer - what name should I give to this pointer: aaa.com \ aaa.net or other name?
2. Some emails are being rejected when sending from both hMailServer and SMTP service - SPF is configured correctly and I'm not blacklisted. I'm getting an NDR message regarding incorrect "HELO" - can anyone put a light on this issue, how and where it should be configured?
(The message I receive is: "Remote server replied: 550 Access denied - Invalid HELO name (See RFC2821 4.1.1.1")

Thanks in advance.
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Britt ThompsonSr. Systems Engineer
Top Expert 2009
Commented:
If your server is going to be sending mail as aaa.com and aaa.net from the same IP you'll need 2 PTR records to ensure you don't get bounce backs from domains that do reverse lookups. You may be able to get away with having a PTR for one or the other domain but it may not work from some receiving servers. Typically, 2 PTR records for the same IP isn't recommended but I see no other way here.

Sounds like don't have the default host name set as the FQDN as the server...not familiar with hMail but there must be a setting to configure the server's name somewhere.
Dave HoweSoftware and Hardware Engineer
Commented:
normally, the sending domain doesn't have to match the helo domain - its common to find mail announced with a helo as from mail.isp.tld accepted for sending mail to vanitydomain.tld provided
a) the ptr record for the IP points to mail.isp.tld
b) (often) the MX record for the domain being sent from includes mail.isp.tld (even as a 9999 record)
c) if there IS a SPF record, it refers to either the server directly or the mx.

so, you should decide what you want the ptr to be, and configure a forward record and both ehlo banner names to suit.
Commented:
Thanks -
Your comments were very helpful.

Finally, the change I did that solved my problem is to change the domain's MX to mail.mydomain.com (instead od an IP address) - and change the FQDN to mail.mydomain.com as well.

This solved the problem immediately.

Author

Commented:
The answers the experts gave me were very helpful, nevertheless, the solution I posted solved my problem.

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