Need to upgrade a 2019 Essentials to 2022 Standard. What will be the best upgrade path? In-place upgrade of 2019 Essentials to 2022 Essentials, then 2022 Essentials to 2022 Standard? (2022 Essentials trial license key works in this case?) Or in-place upgrade from 2019 Essentials to 2019 Standard, and then in-place upgrade again from 2019 Standard to 2022 Standard? Thanks!

Do not do an in-place upgrade. I'd use dcdiag / repadmin tools to verify health correcting all errors found before starting any operations. Then stand up the new 2019 or 2022, patch it fully, license it, join existing domain, add active directory domain services, promote it also making it a GC (recommended), transfer FSMO roles over (optional), transfer pdc emulator role (optional), use dcdiag / repadmin tools to again verify health, when all is good you can decommission / demote old one. --please don't forget to upvote and Accept as answer if the reply is helpful--

There is no 2022 Essentials edition, only Standard and Datacenter (in addition to Azure-based editions)

Windows Server 2019 Essentials to Server 2022 Standard

Accepted answer

Dave Patrick 426K Reputation points MVP

2022-02-15T22:11:26.667+00:00

Do not do an in-place upgrade.

I'd use dcdiag / repadmin tools to verify health correcting all errors found before starting any operations. Then stand up the new 2019 or 2022, patch it fully, license it, join existing domain, add active directory domain services, promote it also making it a GC (recommended), transfer FSMO roles over (optional), transfer pdc emulator role (optional), use dcdiag / repadmin tools to again verify health, when all is good you can decommission / demote old one.

--please don't forget to upvote and Accept as answer if the reply is helpful--
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Dave Patrick 426K Reputation points MVP

2022-02-16T12:50:12.517+00:00

Just checking if there's any progress or updates?

--please don't forget to upvote and Accept as answer if the reply is helpful--

Minghui Yu 21 Reputation points

2022-05-14T19:12:08.587+00:00

Haven't done yet :(

Dave Patrick 426K Reputation points MVP

2022-05-14T19:13:45.487+00:00

Please don't forget to close up the thread by

Minghui Yu 21 Reputation points

2022-05-14T20:36:02.003+00:00

What scares or confused me is this:

https://cloudblogs.microsoft.com/windowsserver/2018/09/05/windows-server-2019-essentials-update/
If configured as a Domain Controller, Windows Server 2019 Essentials must be the only Domain Controller, must run all Flexible Single Master Operations (FSMO) roles, and cannot have two-way trusts with other Active Directory domains.

Does it mean a 2022 Std instance cannot be a DC at all? I didn't explain very clearly at the beginning: there are two physical machines. Machine A is the old server, running 2019 Essentials, as a DC and as a file server; machine B is the new server, to be installed with Win 2022 Std, and will work as the DC. The plan is to promote the new machine to domain controller, and demote the old DC (but the old server will continue to work as a file server).

Dave Patrick 426K Reputation points MVP

2022-05-14T20:43:47.367+00:00

Yes, the Server 2022 can be a domain controller. If I understand correctly the 2019 essentials will become a file server? This may be possible, but you'll likely need to clean install it after the roles are moved to Server 2022 domain controller.
https://learn.microsoft.com/en-us/windows-server-essentials/install/add-windows-server-essentials-as-a-member-server
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Windows Server 2019 Essentials to Server 2022 Standard

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