Hi @HyeongWookKim-7855 ,
What VS you are referring to refers to Virtual directory?
Have you tried using OWA to log in to the user's mailbox?
Do all users have this issue? Or is it for users on a specific version of Exchange?
1.Accroding to my test in lab environment, I changed the URLs of the two Exchange virtual directories to be the same. After the mailboxes in the two Exchanges can be successfully logged in. So the Exchange 2016 and Exchange 2019 server could have the same virtual directory.
2.Regarding F5, I suggest you consult the provider of F5 to check the relevant recommended configuration. When you configure the same environment in the lab environment, did you configure F5?
3.Do you still have an Exchange 2019 server? If so, when the problem recurs, you could following the steps to check whether the autodiscover service work normally. Please make sure that certificate include the correct Subject and SAN. In addition, after making any changes to Virutal direcotry, please run the IISRESET in the Run start as Administrator to restart the IIS.
- Using the ExRca to check the Outlook connection, if any error occurs, a detailed error report will be generated.
For more information: Microsoft Remote Connectivity Analyzer - Run the Test E-mail AutoConfiguration.
4.ccording to the Microsoft official article, it’s not recommend that you disable IPv6 or its components. It’s recommend using “Prefer IPv4 over IPv6” in prefix policier instead fo disabling IPv6. And in Exchange 2013 or later servers fully support IPv6 networks. Therefore, even if you aren't using IPv6, you don't need to disable IPv6 on your Exchange servers.
For more information you could refer to: IPv6 support in Exchange 2013 and Guidance for configuring IPv6 in Windows for advanced users
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