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hassanshakeri's avatar
hassanshakeri
Copper Contributor
Nov 13, 2023
Solved

How to test mail flow in Exchange 2019 in an existing Exchange 2013 environment.(Solved)

Hi experts, I'm trying to complete the upgrade process from Exchange 2013(on-premise) to Exchange 2019(on-premise).   I did all the steps that are explained in Best Practice for Upgrade and the Up...
exchange 2019
Exchange Server
Exchange2013
On-Premise
  • hassanshakeri's avatar
    hassanshakeri
    Dec 07, 2023

    Hi,

    As I finally found and solved the issue, I'd like to share my work with you.

    Maybe in future, some one need to know it.

     

    The issue was so less simple than I thought and was just alternative names in the certificate. I created another SAN self-signed certificate with alternative names like the certificate in our live environment and set it in IIS.

    With this script:

    New-SelfSignedCertificate -DnsName "server1name","server2name","mxRecord","autodiscover.domain.com" -KeyAlgorithm RSA -KeyLength 2048 -CertStoreLocation "Cert:\LocalMachine\My" -NotAfter (Get-Date).AddYears(10) -FriendlyName "certificateName"

     

    After binding the certificate, Outlook works and all errors are gone.

     

    I hope in this Artikel you can find any solution that helps you to solve the same issues.

     

    Regards,

    Hassan

Dan_Snape's avatar
Dan_Snape
Steel Contributor
Nov 14, 2023
When I need to perform functional testing like this I do it from a workstation that has a hosts file that points the DNS names used for mail to the new servers. Make sue you capture all the DNS names used to connect to Exchange in the hosts file
  • hassanshakeri's avatar
    hassanshakeri
    Copper Contributor
    Nov 15, 2023

    Dan_Snape 

    Thanks for your reply. I edited the host file to address Outlook to the new servers before. But it still can not find the servers. I pointed the mx and autodiscover record to the new servers. If there is any other DNS that should be pointed to the new environment?

     

    Kind Regard,

    Hassan

    • Dan_Snape's avatar
      Dan_Snape
      Steel Contributor
      Nov 15, 2023
      Try and do a test using the Outlook Test email auto configuration utility. That will give you some ideas of what might be going wrong. If you've got the host file pointing all DNS names required to the new servers (I'm not able tell you what DNS names you're Exchange environment is using), then I'd say you've got something blocking network connections to the new Exchange servers.
      • hassanshakeri's avatar
        hassanshakeri
        Copper Contributor
        Nov 21, 2023

        Hi Dan_Snape and thanks a lot for the time to answer me.

        What I don't understand is, if my way is the right way. 

        short explanation again:

        There are 2 servers in a domain configured on an LB. ex1 and ex2 in production. So we have an MX record for this area.

        servers : ex1.mydomain.com & ex2.mydomain.com

        mx record: mx.mydomain.com

        autodiscover: autodicover.mydomain.com

         

        Now, I installed 2 new servers as Exchange 2019. What do I want to test? I created some mailboxes on the new servers' databases and I want to test mail flow just on these two servers.

        I have a test laptop and I edited the host file to:

        .

        .

        .

        new server IP   mx.mydomain.com

        new server IP   autodiscover.mydomain.com

        In this way, my goal is that the test laptop will just connect to the new server.

         

        As I on top mentioned, I can connect directly to the servers per browser with 443. But when I run Outlook, I get those errors. This I can not understand.

         

        I'm sorry to bother you with the long post but I appreciate it if you have any ideas here.

         

        Kind regards, 🙂

        Hassan

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