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I've installed SMTP service on Windows Server 2008.

I'm attempting to send emails, however none get delivered. I've scoured logs for a long time, and have solved a few errors.

Currently all emails dropped in the pickup folder are being sent to the badmail folder. The error in the logs is:

Message delivery to the remote domain 'scirra.com' failed for the following reason: Unable to deliver the message because the destination address was misconfigured as a mail loop.

I also downloaded and ran SMTPDiag.exe which gives the following error:

enter image description here

Can anyone help me solve this issue? I'm completely stuck, I've offered to pay our host to fix it but they insist it's all setup correctly. I have a feeling it might be a misconfigured DNS record? I'm not really sure. Thanks for any help.

Here's our DNS info it it helps at all? http://www.intodns.com/scirra.com

Edit, more info

I drop the following file into my pickup folder:

to:scirra@gmx.com
from:noreply@scirra.com
subject:This is a test.

this is a test.

The gmx address is a temp one I've set up for tests. 3 entries pretty much immediately appear in our badmail folder:

.bad file

From: postmaster@WIN-MT04GJ7U5CB.DNSS
To: noreply@scirra.com
Date: Sun, 26 Feb 2012 20:12:47 +0000
MIME-Version: 1.0
Content-Type: multipart/report; report-type=delivery-status;
    boundary="9B095B5ADSN=_01CCF45544F0D21F00000011WIN?MT04GJ7U5CB."
X-DSNContext: 7ce717b1 - 1378 - 00000002 - C00402CF
Message-ID: <FRaqbC8wS00000009@WIN-MT04GJ7U5CB.DNSS>
Subject: Delivery Status Notification (Failure)

This is a MIME-formatted message.  
Portions of this message may be unreadable without a MIME-capable mail program.

--9B095B5ADSN=_01CCF45544F0D21F00000011WIN?MT04GJ7U5CB.
Content-Type: text/plain; charset=unicode-1-1-utf-7

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.

       scirra@gmx.com




--9B095B5ADSN=_01CCF45544F0D21F00000011WIN?MT04GJ7U5CB.
Content-Type: message/delivery-status

Reporting-MTA: dns;WIN-MT04GJ7U5CB.DNSS
Received-From-MTA: dns;WIN-MT04GJ7U5CB.DNSS
Arrival-Date: Sun, 26 Feb 2012 20:12:47 +0000

Final-Recipient: rfc822;scirra@gmx.com
Action: failed
Status: 5.3.5

--9B095B5ADSN=_01CCF45544F0D21F00000011WIN?MT04GJ7U5CB.
Content-Type: message/rfc822

Received: from mail pickup service by WIN-MT04GJ7U5CB.DNSS with Microsoft SMTPSVC;
     Sun, 26 Feb 2012 20:12:47 +0000
to:scirra@gmx.com
from:noreply@scirra.com
subject:This is a test.
Message-ID: <WIN-MT04GJ7U5CBZS2T00000008@WIN-MT04GJ7U5CB.DNSS>
X-OriginalArrivalTime: 26 Feb 2012 20:12:47.0741 (UTC) FILETIME=[02119AD0:01CCF4C3]
Date: 26 Feb 2012 20:12:47 +0000

this is a test.


--9B095B5ADSN=_01CCF45544F0D21F00000011WIN?MT04GJ7U5CB.--

.bdp

Can't tell anything useful from contents of this file

.bdr

Unable to deliver this message because the follow error was encountered: "This message is a delivery status notification that cannot be delivered.".

The specific error code was 0xC00402C7.


The message sender was <>.


The message was intended for the following recipients.
    noreply@scirra.com

Telnet Test

These are the commands I enter into Telnet (responses are in asterix)

telnet localhost 25
helo www.scirra.com
**250 WIN-MT04GJ7U5CB.DNSS Hello [127.0.0.1]**
mail from:noreply@scirra.com
**250 2.1.0 noreply@scirra.com....Sender OK**
rcpt to:scirra@gmx.com
**250 2.1.5 scirra@gmx.com**
data
**354 Start mail input; end with <CRLF>.<CRLF>**
subject: testing email

testing email content

.
**250 2.6.0 <WIN-MT04GJ7U5CBKpCK00000009@WIN-MT04GJ7U5CB.DNSS> Queued mail for delivery**

This creates a badmail file:

From: postmaster@WIN-MT04GJ7U5CB.DNSS
To: noreply@scirra.com
Date: Sun, 26 Feb 2012 20:20:32 +0000
MIME-Version: 1.0
Content-Type: multipart/report; report-type=delivery-status;
    boundary="9B095B5ADSN=_01CCF45544F0D21F00000013WIN?MT04GJ7U5CB."
X-DSNContext: 7ce717b1 - 1378 - 00000002 - C00402CF
Message-ID: <A1XvpFVjC0000000a@WIN-MT04GJ7U5CB.DNSS>
Subject: Delivery Status Notification (Failure)

This is a MIME-formatted message.  
Portions of this message may be unreadable without a MIME-capable mail program.

--9B095B5ADSN=_01CCF45544F0D21F00000013WIN?MT04GJ7U5CB.
Content-Type: text/plain; charset=unicode-1-1-utf-7

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.

       scirra@gmx.com




--9B095B5ADSN=_01CCF45544F0D21F00000013WIN?MT04GJ7U5CB.
Content-Type: message/delivery-status

Reporting-MTA: dns;WIN-MT04GJ7U5CB.DNSS
Received-From-MTA: dns;www.scirra.com
Arrival-Date: Sun, 26 Feb 2012 20:19:43 +0000

Final-Recipient: rfc822;scirra@gmx.com
Action: failed
Status: 5.3.5

--9B095B5ADSN=_01CCF45544F0D21F00000013WIN?MT04GJ7U5CB.
Content-Type: message/rfc822

Received: from www.scirra.com ([127.0.0.1]) by WIN-MT04GJ7U5CB.DNSS with Microsoft SMTPSVC(7.5.7601.17514);
     Sun, 26 Feb 2012 20:19:43 +0000
subject: testing email
From: noreply@scirra.com
Bcc:
Return-Path: noreply@scirra.com
Message-ID: <WIN-MT04GJ7U5CBKpCK00000009@WIN-MT04GJ7U5CB.DNSS>
X-OriginalArrivalTime: 26 Feb 2012 20:20:22.0045 (UTC) FILETIME=[10DAE4D0:01CCF4C4]
Date: 26 Feb 2012 20:20:22 +0000

testing email content



--9B095B5ADSN=_01CCF45544F0D21F00000013WIN?MT04GJ7U5CB.--
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1 Answer

up vote 2 down vote accepted

The error code (5.3.5) refers to a configuration inconsistency that might cause the mail server to loop an email back to itself.

Do you already host an Exchange organization on the server? Or maybe host gmx.com. as a stub zone in your local DNS server?

share|improve this answer
    
I'm not really sure what Exchange organisation is I'm afraid :( All I'm trying to do is get our server to send emails so our website can send emails for forgotten passwords, newsletters etc. Currently we use google apps to receive email for address xyz@scirra.com, we just want now to set our own SMTP server to send emails to people now but they always fail and don't send. We can't use google apps to send mail as we exceed their limits. –  Tom Gullen Feb 26 '12 at 20:55
    
Could our SPF records be stopping it sending? serverfault.com/questions/363362/… Our current server IP is 108.60.144.10/11 –  Tom Gullen Feb 26 '12 at 20:59
    
Try changing the DNS servers used by the server. For example to googles public DNS: code.google.com/speed/public-dns –  Mathias R. Jessen Feb 26 '12 at 20:59
    
@TomGullen The SPF record could very well affect it (which was one of the reasons i suggested you updated it) ;-) –  Mathias R. Jessen Feb 26 '12 at 21:01
    
Ok I've deleted the SPF for now to see if it's the reason, I guess I have to wait a few hours for these changes to work –  Tom Gullen Feb 26 '12 at 21:06
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