Inline upgrade of Exchange Server 2016 into 2019 after the Windows Server upgrade.

Question

Hi Folks,

I need some help and clarification to perform the inline upgrade for both OS and Exchange Server below to the latest edition:

VM1 (Site 1)
Windows Server 2016
Exchange Server 2016

VM1 (Site 2)
Windows Server 2016
Exchange Server 2016

...
VM1 (Site N)
Windows Server 2016
Exchange Server 2016

Inline upgrade:

1. Insert Windows Server 2022 .ISO file and then upgrade the OS.
2. Install Exchange Server 2019 after the Windows Server has been updated to Windows Server 2022.

Can someone please confirm if this is the supported method or must not be done in that way?

There are no mailboxes on-premise running on the Exchange Server 2016 it is just there for the sake of Hybrid Exchange requirements.

https://learn.microsoft.com/en-us/lifecycle/products/exchange-server-2016

Thank you in advance.

Answer 1

Hello,

Upgrade your operating system to Windows Server 2022 before installing Exchange Server 2019. This is consistent with Microsoft's Exchange Server 2016 Product Lifecycle Guidelines and is a supported approach.

However, before proceeding with the upgrade, it is important to ensure that your environment meets the minimum requirements for Windows Server 2022 and Exchange Server 2019. You should also perform a thorough backup of your current environment to ensure you can recover if any issues arise during the upgrade. For more information you can refer to: https://learn.microsoft.com/en-us/windows-server/get-started/upgrade-overview https://learn.microsoft.com/en-us/exchange/plan-and-deploy/supportability-matrix?view=exchserver-2019

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Answer 2

If you can spin new Windows Server 2022 virtual machines from scratch, install Exchange from scratch, and migrate mailboxes, I highly recommend choosing this route instead of performing an in-place upgrade. While Windows Server does a fantastic job in terms of the in-place upgrade process, I wouldn't say the same about Exchange. Unlike pure in-place upgrades, migration does not require any significant downtime, which is another solid argument to go in this direction.