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Delayed Delivery / Non Delivery

Delayed Delivery / Non Delivery

Delayed Delivery / Non Delivery

(OP)
Hi All,

We are running Exchange 2010 SP3 on a Windows 2012 server.

We have been trying to resolve a problem with regards to exchange delivery to a particular domain. Messages with no attachments seem to go through normally, but messages with attachments depending on size can take an hour to 48 hours to deliver due to reattempts.

We tried setting up a separate exchange connector for this specific domain and remove all limits, etc however the problems still persist. It appears that the initial email message is sent to the far end, they are apparently sending back an smtp response but we do not seem to receive or process it and the connection is dropped after exactly 10 minutes.

We only have problems with the 1 particular domain. We can send the same message with attachments fine to a Gmail / Hotmail / etc account with attachments and they go through almost immediately.

Here is a sample from our exchange SMTP logs (slightly modified for forum purposes):

2013-08-13T15:22:30.447Z,Ontario.ca,08D05D22229CC11B,0,,204.41.8.11:25,*,,attempting to connect
2013-08-13T15:22:30.490Z,Ontario.ca,08D05D22229CC11B,1,192.168.1.7:60782,204.41.8.11:25,+,,
2013-08-13T15:22:30.565Z,Ontario.ca,08D05D22229CC11B,2,192.168.1.7:60782,204.41.8.11:25,<,220 smtpgw1.gov.on.ca,
2013-08-13T15:22:30.565Z,Ontario.ca,08D05D22229CC11B,3,192.168.1.7:60782,204.41.8.11:25,>,EHLO mail.somedomain.com,
2013-08-13T15:22:30.606Z,Ontario.ca,08D05D22229CC11B,4,192.168.1.7:60782,204.41.8.11:25,<,250-ESMTP Server Ready,
2013-08-13T15:22:30.606Z,Ontario.ca,08D05D22229CC11B,5,192.168.1.7:60782,204.41.8.11:25,<,250-SIZE 26214400,
2013-08-13T15:22:30.606Z,Ontario.ca,08D05D22229CC11B,6,192.168.1.7:60782,204.41.8.11:25,<,250-DSN,
2013-08-13T15:22:30.606Z,Ontario.ca,08D05D22229CC11B,7,192.168.1.7:60782,204.41.8.11:25,<,250-STARTTLS,
2013-08-13T15:22:30.606Z,Ontario.ca,08D05D22229CC11B,8,192.168.1.7:60782,204.41.8.11:25,<,250 TLS,
2013-08-13T15:22:30.606Z,Ontario.ca,08D05D22229CC11B,9,192.168.1.7:60782,204.41.8.11:25,>,STARTTLS,
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,10,192.168.1.7:60782,204.41.8.11:25,<,220 Server ready Ready to start TLS,
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,11,192.168.1.7:60782,204.41.8.11:25,*,,Sending certificate
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,12,192.168.1.7:60782,204.41.8.11:25,*,CN=mail.somedomain.com,Certificate subject
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,13,192.168.1.7:60782,204.41.8.11:25,*,CN=mail.somedomain.com,Certificate issuer name
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,14,192.168.1.7:60782,204.41.8.11:25,*,3CCD532F11187B884C9F6BCC25A075D1,Certificate serial number
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,15,192.168.1.7:60782,204.41.8.11:25,*,83B8461AB84191BE7857BB5F1000186E8A2F884E,Certificate thumbprint
2013-08-13T15:22:30.646Z,Ontario.ca,08D05D22229CC11B,16,192.168.1.7:60782,204.41.8.11:25,*,mail.somedomain.com,Certificate alternate names
2013-08-13T15:22:30.787Z,Ontario.ca,08D05D22229CC11B,17,192.168.1.7:60782,204.41.8.11:25,*,,Received certificate
2013-08-13T15:22:30.787Z,Ontario.ca,08D05D22229CC11B,18,192.168.1.7:60782,204.41.8.11:25,*,3FE1D2642839A1AF2E44056E2ACB15C6F6DF90D8,Certificate thumbprint
2013-08-13T15:22:30.788Z,Ontario.ca,08D05D22229CC11B,19,192.168.1.7:60782,204.41.8.11:25,>,EHLO mail.somedomain.com,
2013-08-13T15:22:30.884Z,Ontario.ca,08D05D22229CC11B,20,192.168.1.7:60782,204.41.8.11:25,<,250-ESMTP Server Ready,
2013-08-13T15:22:30.884Z,Ontario.ca,08D05D22229CC11B,21,192.168.1.7:60782,204.41.8.11:25,<,250-SIZE 26214400,
2013-08-13T15:22:30.884Z,Ontario.ca,08D05D22229CC11B,22,192.168.1.7:60782,204.41.8.11:25,<,250 DSN,
2013-08-13T15:22:30.885Z,Ontario.ca,08D05D22229CC11B,23,192.168.1.7:60782,204.41.8.11:25,*,4171,sending message
2013-08-13T15:22:30.885Z,Ontario.ca,08D05D22229CC11B,24,192.168.1.7:60782,204.41.8.11:25,>,MAIL FROM:<Test.User@somedomain.com> SIZE=5746583,
2013-08-13T15:22:30.952Z,Ontario.ca,08D05D22229CC11B,25,192.168.1.7:60782,204.41.8.11:25,<,250 +OK Sender OK,
2013-08-13T15:22:30.952Z,Ontario.ca,08D05D22229CC11B,26,192.168.1.7:60782,204.41.8.11:25,>,"RCPT TO:<test.user@ontario.ca> NOTIFY=SUCCESS,FAILURE,DELAY",
2013-08-13T15:22:30.997Z,Ontario.ca,08D05D22229CC11B,27,192.168.1.7:60782,204.41.8.11:25,<,250 +OK Recipient OK,
2013-08-13T15:22:31.081Z,Ontario.ca,08D05D22229CC11B,28,192.168.1.7:60782,204.41.8.11:25,>,DATA,
2013-08-13T15:22:31.122Z,Ontario.ca,08D05D22229CC11B,29,192.168.1.7:60782,204.41.8.11:25,<,"354 Start mail input, end with '<CR><LF>.<CR><LF>' ",
2013-08-13T15:32:33.492Z,Ontario.ca,08D05D22229CC11B,30,192.168.1.7:60782,204.41.8.11:25,-,,Remote


Has anyone else experienced something similar to this? Does anyoen have any ideas how we might be able to resolve this issue?

Thanks!

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