Forum Discussion
hassanshakeri
Nov 13, 2023Copper Contributor
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...
- 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
Nov 15, 2023Steel Contributor
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
Nov 21, 2023Copper 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_SnapeNov 21, 2023Steel ContributorSounds 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.