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Fegume's avatar
Fegume
Copper Contributor
Nov 21, 2023

SmtpResponse: 451 4.4.397 Error comunicating with target host. -> 421 4.2.1 Unable to connect -->

Hello I have:

 

Server Work:

  • Windows Server 2008 R2
  • Exchange 2010

Server with issue:

  • Windows Server 2016
  • Exchange 2016

Domain: Windows Server 2016

 

I try migrate my Exchange 2010 to Exchange 2016. I can't move mailbox, beacause Exchange Server 2016 cannot send mails. Only Exchange 2010 can send email.

 

Test:

 

Exchange 2010 to Exchange 2016 -->OK

Exchange 2010 to 2010--> OK

Exchange 2016 to 2010--> Failed

Exchange 2016 to 2016 --> Failed

 

My Environment is only to send emails within my domain, the send connector are identity Exchange 2010 and 2016, but when I try send a email with user on database Exchange 2016 to same user, not received.

 

I try look any logs and view this:

 

DiagnosticInfo= Error: RetrySmtp, Diagnostic Information: Stage: UpdateMsgIdToPoisonContextMapping, SmtpResponse: 451 4.4.397 Error comunicating with target host. -> 421 4.2.1 Unable to connect -->SocketConnections Refused: Socket error code 10061, details;FailedRecipientCount:0, RetryRecipientCount:0; S:DeliveryPriority=Normal", Email, f1c83-5234-.................., 15.01.2106.008

 

I disabled firewall and antivirus, but the problem is the same.

 

Any idea is good! 

 

Regards!

8 Replies

    • Fegume's avatar
      Fegume
      Copper Contributor
      Hello, @TAE YOU ANN

      Yes the anti-spam is work on Exchange 2010.
      This razon posibility solution for this:
      Exchange 2016 to 2010--> Failed

      but. why can't send email on users the same mailboxdatabase?.
      This example :
      Exchange 2016 to 2016 --> Failed

      Regards!
      • Fegume 

        Please review the hosts file in the C:\Windows\System32\drivers\etc path!
        If there are unnecessary values, remove them and try again!

        Case) If the value of Exchange Server is registered, it needs to be removed.

  • Dan_Snape's avatar
    Dan_Snape
    Bronze Contributor
    Check if your new Exchange server IP address is listed in one of your custom receive connectors.
    • Fegume's avatar
      Fegume
      Copper Contributor

      Hi Dan_Snape ,

       

      Received connector Exchange server 2010 allow all.

      The problem is more simple, is on Exchange 2016. I have one mailboxdatabase with one user, mailto:user1@domain.local. 

       

      the user1 is configure on my outook. I try send email:

      from:  mailto:user1@domain.local.

      to: mailto:user1@domain.local

       

      The email no received, but I try send to Exchange 2010 users, same problem.

       

      I try Send user on mailboxdatabase on Exchange 2010 to mailto:user1@domain.local and the email yes received.

       

      Regards!

      • Dan_Snape's avatar
        Dan_Snape
        Bronze Contributor
        I'm not sure whether your reply means you have Exchange servers in a custom receive connector or not. You should never put Exchange server infrastructure (ie Exchange server IPs) in a custom receive connector as this may break mail flow similar to what you are experiencing. The default receive connectors are designed to handle internal mail flow between Exchange servers securely and without any requirements for admins to make any changes

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