troubleshooting Question

The message reached the recipient's e-mail system, but delivery was refused. Attempt to resend the message. If it still fails, contact your system administrator. <Backendserver.domain.net #5.2.1>

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One of our users uses CRM to track emails to cases, when an email is sent using the tracking facility of CRM via the Outlook plugin to one of our other users the message gets NDR'ed back with the following NDR:

Your message
  To:      Recipient Name
  Subject:      Email tracked in CRM
  Sent:      Fri, 23 May 2008 13:28:03 +0100

did not reach the following recipient(s):
Recipient Name on Fri, 23 May 2008 13:29:06 +0100
The message reached the recipient's e-mail system, but delivery was refused.  Attempt to resend the message.  If it still fails, contact your system administrator.
<Backendserver.domain.net #5.2.1>

I replaced the recipient names and server name for security reasons.

Oddly when the same sender sends an email from Outlook without using the CRM tracking to the same the message gets delivered without a problem

Both sender and recipient use our services and they are both on the same back-end server.

They are also both users and not public folders as much of my searching seems to associate the 5.2.1 error with public folders or disabled accounts. I have checked and the recipient is not disabled in any way and is receiving mail from other senders without problems.

Message Tracking the email that NDR's gives the following:

Event Date/Time - SMTP Store Driver: Message Submitted from Store - Event ID 1027
Event Date/Time - SMTP: Message Submitted to Advanced Queueing - Event ID 1019
Event Date/Time - SMTP: Started Message Submission to Advanced Queue - Event ID 1025
Event Date/Time - SMTP: Message Submitted to Categorizer - Event ID 1024
Event Date/Time - SMTP: Message Categorized and Queued for Routing - Event ID 1033
Event Date/Time - SMTP: Message Queued for Local Delivery - Event ID 1036
Event Date/Time - SMTP: Message Delivered Locally to recipient@email.com - Event ID 1023
Event Date/Time - SMTP: Non-Delivered Report (NDR) Generated - Event ID 1030

We enabled diagnostic logs for a time to see what event log was saying on it and got this error:

The following call : EcSetFileHandleProp to the store failed. Error code : -2147219200 (Message will be NDR'd). MDB : c2c1d522-f0b8-44ba-8b01-1bf5646bd7cc. FID : . MID : . File : J:\EXCHSRVR\Mailroot\vsi 1\Queue\NTFS_9d1adf6f01c8ab7b001233ee.EML.

Which lead us to this MS KB article:

http://support.microsoft.com/kb/926347

The only thing odd about the From: field of the sender though is that the name is contained in quotation marks i.e "Firstname Lastname" <Email@address.com>

Headers from an email tracked in CRM that NDR'ed:

X-MimeOLE: Produced By Microsoft Exchange V6.5
Content-Class: urn:content-classes:message
MIME-Version: 1.0
Content-Type: multipart/related;
      boundary="----_=_NextPart_004_01C8BCD0.727467F0";
      type="multipart/alternative"
Subject: Email tracked in CRM
Date: Fri, 23 May 2008 13:28:03 +0100
Message-ID: <7A9662AF-C328-DD11-9E25-005056C00008>
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator:
Thread-Topic: Email tracked in CRM
Thread-Index: Aci80HG1ScqBvMHDTTKJd6K92Fyzig==
From: "Firstname Lastname" <email@address.com>
To: <recipient@address.com>

Headers from a mail that was not tracked and was delivered:

X-MimeOLE: Produced By Microsoft Exchange V6.5
Content-Class: urn:content-classes:message
MIME-Version: 1.0
Content-Type: multipart/related;
      boundary="----_=_NextPart_006_01C8BCD0.4C564200";
      type="multipart/alternative"
Subject: Email not tracked
Date: Fri, 23 May 2008 13:27:52 +0100
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator:
Thread-Topic: Email not tracked
Thread-Index: Aci80Gu9e/E2B/ReR9+QkXNfZmoOFw==
From: "Firstname Lastname" <email@address.com>
To: <recipient@address.com>

Anyone have any ideas on anything further we can check here?

Regards,
Chris
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