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I'm trying to diagnose why emails I'm sending out from my server's IIS SMTP Pickup Folder are getting bounced back occasionally.

One tech from a receiving company who couldn't receive the emails said:

The email would go through if you could configure your server to use
<servername>.<domain>.<tld> instead of just <servername>

I navigated to the following place in IIS:

  • Internet Information Services
    • myservername (local computer)
      • Default SMTP Virtual Server
        • Domains

Once there, I see I can rename the Domain Name to be anything I want. I've done that, but now I'm trying to figure out if it is enough.

Once I send out a test email, here is the antispam report I see from gmail, for example:

    CIP:<server ip>;
    H:<server name>;
    RD:<server name>.<domain>.<tld>;

I'm trying to figure out what any of this means, so I know if I've configured it properly. What's the difference between H and RD? Is there some sort of ForeFront Antispam documentation that describes what the different codes mean?

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  • "H:" is the host name - name assigned to the server
  • "RD:" appears to be the Fully Qualified Domain Name (FQDN)

This is actually more of a SMTP server configuration situation as to how your server is "announcing" itself to the other servers when they negotiate SMTP sessions. It just happens to be "ForeFront" being your system that ultimately "connects" with the external SMTP systems.

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The main problem you're having here (with spam or SMTP bouncebacks) will be that the server you're sending mail from isn't an Internet SMTP server, and therefore doesn't have any of the proper mail records registered against it should someone do a DNS lookup and IP reverse lookup.

Unfortunately most SMTP servers trawl back on all SMTP servers that the email has gone through before it received it, and if any of those don't check out as being "legitimate" then they will deny and drop or bounce the email.

Look at something like SPF:

Or it might be a good idea to have the originating server not send emails itself, and to use a properly configured SMTP server in your organisation like Exchange or an external SMTP provider who allows you relay.

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