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Luigi avatar Server

I can't send mail from Exchange 2010 to 2003 (coexistence)

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Luigi

I have an error when sending mail from 2010 to 2003 coexistence:

error 550 4.4.7 queue expired; message expired

This is the version I use to test

Ex2003 |  v6.5 Build 7638.2 SP2    |       6.5.6500.0

Ex2010 |  v14.3 Build 123.4 SP3    |       8.0.535.0

Testing to upgrade Exchange 2003 to 2010. Reference Exchange upgrade guide

There are problems with one of the RGC (Routing Group Manager) connectors, the connector was created again but the same problem continues.

These are the tests that were carried out to send mail:

source destiny status mail
Ex2003 External OK
Ex2003 Ex2010 OK
Ex2010 Ex2003 does not send
Ex2010 External OK

Reviewing the logs and trying to find any error messages

  1. Event Viewer no error.
  2. Send queue, there is no error (it is pending).
  3. Exchange log, shows error that it did not send 4.4.7 relay.

Checking the possible errors caused by NDR 4.4.7 (MX, DNS, AD, NSLookup) is fine.

  1. How can I test the connection between the Exchange Servers?.
  2. What logs in ASDEdit should I check if the logs are okay?.
  3. What other reason can cause error 550 4.4.7 queue expired message expired?
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Pimp Juice IT avatar
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Pimp Juice IT
Wouldn't that be a send connector things on the Exchange 2010 to ensure it points to Exchange 2003 for the domain(s) it hosts? I'm decommissioning an Exchange 2010 server at the current moment almost fully got them over to Exchange Online, but Exchange 2003 it has been years since I've played with one of those. I think the send connector may be a good starting point to check on the 2010 server or the receive connector accepts from 2010 perhaps is 2003 has receive connector or something related, check its settings too. **Recap:** Check 2010 send connector(s) & 2003 receive connector(s)
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Luigi avatar Server
cn flag
Luigi

We want to migrate Exchange 2003 to 2019, with exchange 2010 as a temporary bridge.

Thanks for the info Joy Zhang, I was reading all the documentation, I'm done running the tests and I'll let you know how it went.
Thanks for the advice Pimp Juice IT, looking for information to test connectors between exchanges.

  1. Exchange 2003, Winroute is a very good tool to see the states of the connectors.
  2. Exchange 2010, I did not find a tool or way to review the connectors, I decided to enable SMTP logs for sending and try to see any errors and Exchange 2003 I did not find logs similar to Exchange 2010.

The curious thing that I saw in the logs, the same EX2010 closes the connection and doing the same with telnet sends the mail without problem to EX2003.

I am looking for information that can cause the connection to close in the connector.

The mail is in queue pending to send with connector send.
error 550 4.4.7 queue expired; message expired

Send Mail From Exchange 2010 to Exchange 2003

---------------------------------------------
                     Telnet                             |               Connector Send
---------------------------------------------

220 EX2003.CONTOSO.COM                                  |   EX2010:15119,EX2003:25,<,   "220 EX2003.CONTOSO.COM,
ehlo EX2010.CONTOSO.COM                                 |   EX2010:15119,EX2003:25,>,   EHLO EX2010.CONTOSO.COM,
250-EX2003.CONTOSO.COM Hello [EX2010.CONTOSO.COM]       |   EX2010:15119,EX2003:25,<,   250-EX2003.CONTOSO.COM Hello [EX2010],
250-TURN                                                |   EX2010:15119,EX2003:25,<,   250-TURN,
250-SIZE                                                |   EX2010:15119,EX2003:25,<,   250-SIZE,
250-ETRN                                                |   EX2010:15119,EX2003:25,<,   250-ETRN,
250-PIPELINING                                          |   EX2010:15119,EX2003:25,<,   250-PIPELINING,
250-DSN                                                 |   EX2010:15119,EX2003:25,<,   250-DSN,
250-ENHANCEDSTATUSCODES                                 |   EX2010:15119,EX2003:25,<,   250-ENHANCEDSTATUSCODES,
250-8bitmime                                            |   EX2010:15119,EX2003:25,<,   250-8bitmime,
250-BINARYMIME                                          |   EX2010:15119,EX2003:25,<,   250-BINARYMIME,
250-CHUNKING                                            |   EX2010:15119,EX2003:25,<,   250-CHUNKING,
250-VRFY                                                |   EX2010:15119,EX2003:25,<,   250-VRFY,
250-X-LINK2STATE                                        |   EX2010:15119,EX2003:25,<,   250-X-LINK2STATE,
250-XEXCH50                                             |   EX2010:15119,EX2003:25,<,   250-XEXCH50,
250 OK                                                  |   EX2010:15119,EX2003:25,<,   250 OK,
mail from:[email protected]                          |   EX2010:15119,EX2003:25,>,   QUIT,
250 2.1.0 [email protected] OK             |   EX2010:15119,EX2003:25,<,   221 2.0.0 EX2003.CONTOSO.COM Service closing transmission channel,
rcpt to:[email protected]                            |   EX2010:15119,EX2003:25,-,,  Local
250 2.1.5 [email protected]                          |
data                                                    |
354 Start mail input; end with <CRLF>.<CRLF>            |
subject:test                                            |
test                                                    |
.                                                       |
250 2.6.0 <[email protected]> |
           Queued mail for delivery                     |
quit                                                    |
221 2.0.0 EX2003.CONTOSO.COM                            |
          Service closing transmission channel          |
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Luigi avatar Server
cn flag
Luigi

Checking the exchange 2010 logs, in connectivity logging there is an error.

2022-10-28T00:23:56.384Z    08DAB85734C516DE    SMTP    cn=first routing group,cn=routing groups,cn=first administrative group,cn=administrative groups,cn=contoso,cn=microsoft exchange,cn=services,cn=configuration,dc=contoso,dc=com >   ex2003.contoso.com[192.168.0.40]
2022-10-28T00:23:56.392Z    08DAB85734C516DE    SMTP    cn=first routing group,cn=routing groups,cn=first administrative group,cn=administrative groups,cn=contoso,cn=microsoft exchange,cn=services,cn=configuration,dc=contoso,dc=com >   Established connection to 192.168.0.40
2022-10-28T00:23:56.394Z    08DAB85734C516DE    SMTP    cn=first routing group,cn=routing groups,cn=first administrative group,cn=administrative groups,cn=contoso,cn=microsoft exchange,cn=services,cn=configuration,dc=contoso,dc=com -   Messages: 0 Bytes: 0 (Retry : Cannot achieve Exchange Server authentication)
2022-10-28T00:33:56.399Z    08DAB85734C516E1    SMTP    cn=first routing group,cn=routing groups,cn=first administrative group,cn=administrative groups,cn=contoso,cn=microsoft exchange,cn=services,cn=configuration,dc=contoso,dc=com +   SmtpRelayToTiRg 4a8c89c9-d854-47fc-91a1-d28d07849dda;QueueLength=28
2022-10-28T00:33:56.399Z    08DAB85734C516E1    SMTP    cn=first routing group,cn=routing groups,cn=first administrative group,cn=administrative groups,cn=contoso,cn=microsoft exchange,cn=services,cn=configuration,dc=contoso,dc=com >   ex2003.contoso.com[192.168.0.40]
2022-10-28T00:33:56.402Z    08DAB85734C516E1    SMTP    cn=first routing group,cn=routing groups,cn=first administrative group,cn=administrative groups,cn=contoso,cn=microsoft exchange,cn=services,cn=configuration,dc=contoso,dc=com >   Established connection to 192.168.0.40

Looking for the error it shows in logs.

Cannot achieve Exchange Server authentication
451 5.7.3 Cannot achieve Exchange Server authentication

The error was found and it was solved with the following guide of the error 451 5.7.3.

  1. configure options SMTP Virtual Server, Port 25
  2. Make sure Integrated Windows Authentication is checked

Thank you very much for the advice, I hope this helps you to update your mail server.

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Joy Zhang avatar Server
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Joy Zhang

A similar thread for your reference: 550 4.4.7 QUEUE.Expired; message expired ##

Since the exchange 2003 and exchange 2010 are not support, you'd better migrate all exchange 2003 mailboxes to exchange 2010 then go to exchange 2016/2019 or exchange online. Detailed steps for you reference: how to migrate exchange 2003 to 2016 including active directory renaming please help

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