Exchange emails not delivering for one user
- by Cylindric
We have an Exchange infrastructure going through a migration from 2003 SP2 (call it ExOld) to 2010 (ExNew).
All users are now on the new server, but mail is still being directed to ExOld until testing is complete. ExNew sends emails directly to the internet.
For one particular user, emails don't seem to be being reliably delivered, but the odd thing is that it's not all emails. I can see external emails in his inbox.
If I send an internal email it works fine.
If I send an email from Gmail to him it doesn't get through.
If I telnet from outside to ExOld I can send an email to him.
If I telnet from outside to ExNew I can send an email to him.
This is a transcript that results in a successful send:
220 ExOldName Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Mon, 22 Oct 2012 10:55:26 +0100
EHLO test.com
500 5.3.3 Unrecognized command
EHLO test.com
250-ExOldFQDN Hello [MyTestExternalIp]
250-TURN
250-SIZE
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-X-EXPS GSSAPI NTLM LOGIN
250-X-EXPS=LOGIN
250-AUTH GSSAPI NTLM LOGIN
250-AUTH=LOGIN
250-X-LINK2STATE
250-XEXCH50
250 OK
MAIL FROM:[email protected]
250 2.1.0 [email protected] OK
RCPT TO:[email protected] notify=success,failure
250 2.1.5 [email protected]
DATA
354 Start mail input; end with .
Subject:Test 1056
Test 10:56
.
250 2.6.0 Queued mail for delivery
quit
221 2.0.0 ExOldFQDN Service closing transmission channel
Emails go through Symantec Cloud, but their "Track and Trace" shows the messages going through, with a "delivered ok" log entry.
2012-10-22 09:19:56 Connection from: 209.85.212.171 (mail-wi0-f171.google.com)
2012-10-22 09:19:56 Sending server HELO string:mail-wi0-f171.google.com
2012-10-22 09:19:56 Message id:CAE5-_4hzGpY2kXFbzxu7gzEUSj5BAvi+BB5q1Gjb6UUOXOWT3g@mail.gmail.com
2012-10-22 09:19:56 Message reference: 135089759500000177171130001194006
2012-10-22 09:19:56 Sender: [email protected]
2012-10-22 09:19:56 Recipient: [email protected]
2012-10-22 09:20:26 SMTP Status: OK
2012-10-22 09:19:56 Delivery attempt #1 (final)
2012-10-22 09:19:56 Recipient server: ExOldIP (ExOldIP)
2012-10-22 09:19:56 Response: 250 2.6.0 Queued mail for delivery
I'm not sure where to look on the old (or new) server for information as to where the mails are ending up.
