Hi @Micheal Mallo ,
Welcome to the Microsoft Q&A platform!
Based on your description, if you want to upgrade from Exchange 2016 to Exchange 2019, the recommended approach is to create a new Exchange 2019 server, migrate mailboxes, and then decommission the Exchange 2016 server12. This approach ensures a smoother transition and minimizes disruption to service.
Refer to:
- https://techcommunity.microsoft.com/t5/exchange-team-blog/upgrading-your-organization-from-current-versions-to-exchange/ba-p/4241305
- https://techcommunity.microsoft.com/t5/exchange-team-blog/upgrading-your-organization-from-current-versions-to-exchange/ba-p/4241305
Microsoft does not support in-place upgrades from Exchange 2016 to Exchange 2019. This process involves setting up a new Exchange 2019 server to coexist with the existing Exchange 2016 environment, migrating mailboxes and other data, and then gradually decommissioning the old server.
Please feel free to contact me for any updates. And if this helps, don't forget to mark it as an answer.
Best,
Jake Zhang