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hassanshakeri's avatar
hassanshakeri
Copper Contributor
Nov 13, 2023

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

LeonPavesic's avatar
LeonPavesic
Silver Contributor
Nov 13, 2023

Hi hassanshakeri,

regarding your question, you can use the Test-Mailflow Powershell cmdlet to diagnose whether mail can be successfully sent from and delivered to the system mailbox on a Mailbox server.

You can also use this cmdlet to verify that email is sent between Mailbox servers within a defined latency threshold.

Here are the steps to test mail flow in Exchange 2019 in an existing Exchange 2013 environment:


Open the Exchange Management Shell on the Exchange 2019 server.
Run the following command:

Test-Mailflow -TargetEmailAddress <email_address>


Replace <email_address> with the email address of the recipient mailbox.
Verify that the test message was delivered to the recipient mailbox.

You can also use the Test-OutlookConnectivity cmdlet to test Outlook connectivity. Here are the steps to test Outlook connectivity:

Open the Exchange Management Shell on the Exchange 2019 server.
Run the following command:

Test-OutlookConnectivity -ProbeIdentity OutlookSelfTestProbe


Verify that the test was successful.

Test-Mailflow (ExchangePowerShell) | Microsoft Learn
Best Practices for Migrating from Exchange Server 2013 to Exchange Server 2019 - Microsoft Community Hub
Mail Flow issues after mailbox migration Exchange 2013 to 2019 (spiceworks.com)

Please click Mark as Best Response & Like if my post helped you to solve your issue.
This will help others to find the correct solution easily. It also closes the item.


If the post was useful in other ways, please consider giving it Like.


Kindest regards,


Leon Pavesic
(LinkedIn)

  • hassanshakeri's avatar
    hassanshakeri
    Copper Contributor
    Nov 14, 2023

    Hi LeonPavesic 


    thanks a lot for your answer. But it seems my question was not clear.
    The mail flow is working fine and all emails are sending and receiving between mailboxes in both server environments. I can test and check them in OWA.
    The problem is, when I create a profile for Outlook in the Mail option in the control panel, and then I Open the Outlook app, it can not find the new servers to connect. It stays there for a long and at the end tells me in an error, that I can not find the proxy server security.

     

    Outlookselftest from the new servers has successful results. 🙄

    This is my main issue and I can not find the reason why Outlook can not find the servers. Is there something wrong with the configurations? I have no more idea.

    I compared all settings between old and new servers and all seem right.

     

    Best,

    Hassan

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