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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

hassanshakeri's avatar
hassanshakeri
Copper Contributor

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

Dan_Snape's avatar
Dan_Snape
Steel Contributor
Nov 21, 2023
Sounds right, but I'm not sure why you are getting the errors. It could be a bunch of misconfiguration, but to me it sounds like your network (ie firewalls, LBs, network devices, proxy) is blocking client traffic in some way. as I said, the Outlook Test email auto configuration utility will give some details of why Outlook is failing.

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