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I am a developer currently struggling with a system administration task so beware of some gaps in my knowledge about things that may seem obvious.

I want to enable SMTP on a Windows Server 2008 R2 VM that's part of a domain with a DC on another VM. I add the feature, it installs well but SMTP is not working. When I try to send email (programmatically, telnet, text file in Pickup folder) it's not working - I don't get error messages, just the email is not being sent.

Upon further inspection I noticed that the files from the Pickup folder (c:\intetpub\mailroot\Pickup) are getting picked up and end up in Queue. The event log doesn't show any abnormalities.

I run SmtpDiag and it shows some failures but we're now speaking about DNS, MX records and SOA and my knowledge doesn't go that far to identify the underlying cause, so I'm sharing the SmtpDiag response with you gurus and hope that you can help me out.

C:\Programs>smtpdiag "xxxx@yyyy.test" "zzzz@gmail.com" /v

Searching for Exchange external DNS settings.
Computer name is aaaa.

Checking SOA for gmail.com.
Checking external DNS servers.
Checking internal DNS servers.

Checking TCP/UDP SOA serial number using DNS server [10.50.130.11].
TCP test succeeded.
UDP test succeeded.
Serial number: 1464827

Checking TCP/UDP SOA serial number using DNS server [10.50.130.13].
Failed: DNS server [10.50.130.13] may be down.
DNS server [10.50.130.13] did not return a valid SOA record.
SOA serial number match: Failed with one or more failures.

Checking local domain records.
Starting TCP and UDP DNS queries for the local domain. This test will try to
validate that DNS is set up correctly for inbound mail. This test can fail for
3 reasons.
    1) Local domain is not set up in DNS. Inbound mail cannot be routed to
local mailboxes.
    2) Firewall blocks TCP/UDP DNS queries. This will not affect inbound mail,
but will affect outbound mail.
    3) Internal DNS is unaware of external DNS settings. This is a valid
configuration for certain topologies.
Checking MX records using TCP: easa.test.
  A:     yyyy.test [10.50.130.11]
  A:     yyyy.test [10.50.130.155]
  A:     yyyy.test [10.50.130.12]
Checking MX records using UDP: easa.test.
  A:     yyyy.test [10.50.130.11]
  A:     yyyy.test [10.50.130.12]
  A:     yyyy.test [10.50.130.155]
Both TCP and UDP queries succeeded. Local DNS test passed.

Checking remote domain records.
Starting TCP and UDP DNS queries for the remote domain. This test will try to
validate that DNS is set up correctly for outbound mail. This test can fail for
3 reasons.
    1) Firewall blocks TCP/UDP queries which will block outbound mail. Windows
2000/NT Server requires TCP DNS queries. Windows Server 2003 will use UDP
queries first, then fall back to TCP queries.
    2) Internal DNS does not know how to query external domains. You must
either use an external DNS server or configure DNS server to query external
domains.
    3) Remote domain does not exist. Failure is expected.
Checking MX records using TCP: gmail.com.
  MX:    alt4.gmail-smtp-in.l.google.com (40)
  MX:    alt3.gmail-smtp-in.l.google.com (30)
  MX:    alt1.gmail-smtp-in.l.google.com (10)
  MX:    alt2.gmail-smtp-in.l.google.com (20)
  MX:    gmail-smtp-in.l.google.com (5)
  A:     gmail-smtp-in.l.google.com [209.85.229.26]
Checking MX records using UDP: gmail.com.
  MX:    alt3.gmail-smtp-in.l.google.com (30)
  MX:    alt1.gmail-smtp-in.l.google.com (10)
  MX:    alt2.gmail-smtp-in.l.google.com (20)
  MX:    gmail-smtp-in.l.google.com (5)
  MX:    alt4.gmail-smtp-in.l.google.com (40)
Both TCP and UDP queries succeeded. Remote DNS test passed.
  A:     alt4.gmail-smtp-in.l.google.com [209.85.225.26]
  A:     alt3.gmail-smtp-in.l.google.com [74.125.127.27]
  A:     alt1.gmail-smtp-in.l.google.com [74.125.39.27]
  A:     alt2.gmail-smtp-in.l.google.com [74.125.43.27]

Checking MX servers listed for zzzz@gmail.com.
Connecting to gmail-smtp-in.l.google.com [209.85.229.26] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gmail-smtp-in.l.google.com.
Connecting to alt1.gmail-smtp-in.l.google.com [74.125.39.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to alt1.gmail-smtp-in.l.google.com.
Connecting to alt2.gmail-smtp-in.l.google.com [74.125.43.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to alt2.gmail-smtp-in.l.google.com.
Connecting to alt3.gmail-smtp-in.l.google.com [74.125.127.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to alt3.gmail-smtp-in.l.google.com.
Connecting to alt4.gmail-smtp-in.l.google.com [209.85.225.26] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to alt4.gmail-smtp-in.l.google.com.

C:\Programs>

SmtpDiag highlights the erros in red and makes the output much more readable - here are just the red parts, listed separately for similar reasons:

Failed: DNS server [10.50.130.13] may be down.
DNS server [10.50.130.13] did not return a valid SOA record.
SOA serial number match: Failed with one or more failures.
...
Connecting to the server failed. Error: 10061
Failed to submit mail to gmail-smtp-in.l.google.com.
...
Connecting to the server failed. Error: 10061
Failed to submit mail to alt1.gmail-smtp-in.l.google.com.
etc...

I tried with other recipients too, including the company email, so it's not just a matter of gmail not being happy with our domain. I'm still worried that a domain name ending with .test may be universally unacceptable - do you think this might be the cause?

share|improve this question
    
It looks like DNS resolution is not functioning properly; are you able to use DIG or NSLOOKUP to get the SOA record (from this server) for gmail.com? –  Coding Gorilla Oct 11 '11 at 17:11
    
Not quite sure how this is done but I did the following: C:\>nslookup/ Default Server: xxxx.yyyy.test/ Address: 10.50.130.11/ >set type=SOA/ >gmail.com/ Server: xxxx.yyyy.test/ Address: 10.50.130.11/ Non-authoritative answer:/ gmail.com/ primary name server = ns1.google.com/ responsible mail addr = dns-admin.google.com/ serial = 1464827/ refresh = 21600 (6 hours)/ retry = 3600 (1 hour)/ expire = 1209600 (14 days)/ default TTL = 300 (5 mins)/ ns1.google.com internet address = 216.239.32.10/ –  Vroomfundel Oct 12 '11 at 10:03
    
Digging a bit deeper, I noticed that the DNS server MX record points to the DC, while I'm setting up the email server on another machine - I guess this means that I won't be able to receive mail on that machine until this is updated. Could this cause problems with sending too? I don't see why would my SMTP server need MX records on the local domain pointing to itself but as I said I'm a beginner in this field. –  Vroomfundel Oct 12 '11 at 11:58
    
No, MX records (of your own) won't have any effect on outgoing mail. I did notice that your NSLOOKUP used the DNS address of 10.50.130.11, but your error messages indicate that it was trying to use DNS 10.50.130.13. Is .13 a DNS server? –  Coding Gorilla Oct 12 '11 at 12:41
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