Several years ago I saw similar behavior with a particular external company. The messages that failed we discovered were sent using "Outlook Rich Text" format. I am not sure what was causing the nk2 entry to be set that way, however in our case the below steps resolved the problem for this client.
To resolve this we deleted the entry from the client's Outlook nickname cache. Then created a contact in that clients Outlook for this external recipient. Once the SMTP address is entered double click it and ensure that it is set to "Let Outlook decide the best sending format". Then send a message selecting the contact from Outlook to ensure that the nk2 file is set to use that contact entry. All future messages using the nk2 entry or the contact were then sent and received successfully for this external company. Hope that helps. Peter Dahl. -----Original Message----- From: Howard Bock [mailto:[EMAIL PROTECTED] Sent: Tuesday, August 26, 2008 1:31 PM To: MS-Exchange Admin Issues Subject: Sporadic NDR's on emails sent to one person. Has anyone witnessed these types of bounce backs? I'm receiving the bounce back when I try to send an email to a specific client. As strange as it sounds it usually gets bounced back when I use the auto complete feature in Outlook 2003. When I delete the auto complete entry and then reenter the email address by hand the email usually goes through to the recipient without a problem. I have deleted the Outlook.NK2 file and I still have the problem. I am running Windows 2003 Small Business Server with Exchange 2003. Listed below is the NDR that I receive when the email does not go through followed by the header information of that email. Please notice that the second line of the email header information is “From: [EMAIL PROTECTED] This leads me to believe that the email is getting bounced back from my Exchange 2003 server. Any help will be greatly appreciated. Thanks, Howard Your message did not reach some or all of the intended recipients. Subject: FW: Maintenance renewal for CT Remote. Sent: 8/17/2008 3:52 PM The following recipient(s) could not be reached: [EMAIL PROTECTED] on 8/17/2008 3:52 PM There was a SMTP communication problem with the recipient's email server. Please contact your system administrator. <mydomain.com #5.5.0 smtp;554 <[EMAIL PROTECTED]>: Relay access denied> ------------------------------------------- Email Header Information ------------------------------- Microsoft Mail Internet Headers Version 2.0 From: [EMAIL PROTECTED] To: [EMAIL PROTECTED] Date: Sun, 17 Aug 2008 15:52:26 -0500 MIME-Version: 1.0 Content-Type: multipart/report; report-type=delivery-status; boundary="9B095B5ADSN=_01C90017BA021EDE00000027mydomain.com" X-DSNContext: 7ce717b1 - 1194 - 00000002 - 00000000 Message-ID: <[EMAIL PROTECTED]> Subject: Delivery Status Notification (Failure) --9B095B5ADSN=_01C90017BA021EDE00000027mydomain.com Content-Type: text/plain; charset=unicode-1-1-utf-7 --9B095B5ADSN=_01C90017BA021EDE00000027mydomain.com Content-Type: message/delivery-status --9B095B5ADSN=_01C90017BA021EDE00000027mydomain.com Content-Type: message/rfc822 Subject: FW: Maintenance renewal for CT Remote. Date: Sun, 17 Aug 2008 15:52:02 -0500 Message-ID: <[EMAIL PROTECTED]> MIME-Version: 1.0 Content-Type: multipart/alternative; boundary="----_=_NextPart_001_01C900AB.1DF6833E" X-MS-Has-Attach: X-MS-TNEF-Correlator: Thread-Topic: Maintenance renewal for CT Remote. Content-class: urn:content-classes:message thread-index: AcjmhWC1zOCrIs+RSoyaUEP+/c2N+AaJVqZg X-MimeOLE: Produced By Microsoft Exchange V6.5 From: "John Doe" <[EMAIL PROTECTED]> To: <[EMAIL PROTECTED]> ------_=_NextPart_001_01C900AB.1DF6833E Content-Type: text/plain; charset="US-ASCII" Content-Transfer-Encoding: quoted-printable ------_=_NextPart_001_01C900AB.1DF6833E Content-Type: text/html; charset="US-ASCII" Content-Transfer-Encoding: quoted-printable ------_=_NextPart_001_01C900AB.1DF6833E-- --9B095B5ADSN=_01C90017BA021EDE00000027mydomain.com— ~ Ninja Email Security with Cloudmark Spam Engine Gets Image Spam ~ ~ http://www.sunbeltsoftware.com/Ninja ~ This communication is confidential and may be legally privileged. If you are not the intended recipient, (i) please do not read or disclose to others, (ii) please notify the sender by reply mail, and (iii) please delete this communication from your system. Failure to follow this process may be unlawful. Thank you for your cooperation. ~ Ninja Email Security with Cloudmark Spam Engine Gets Image Spam ~ ~ http://www.sunbeltsoftware.com/Ninja ~
