Upgrading server 2016 essentials to server 2022 standard

Copper Contributor

I have a few questions about upgrading my on prem server. 


It is currently running 2016 server essentials. It is acting as the local domain controller, as all essentials servers must.


I have acquired server 2022 standard license through my visual studio license benefits, which is pretty cool.


I downloaded the server 2022 installer and started it - hit next a few times, no errors upgrade came up, input the license given to me from the visual studio product keys area: and the installer validated the license, so it seems the license is valid and it technically will do an in-place upgrade. 


This is as far as I chose to go with the installer.


My concerns are:

1) Will I lose any functionality going from 2016 essentials to 2022 standard? Since the server currently acts as local domain controller...all username are like "[businessName].local" - that said, we do have a verified domain name that i intend to connect with Azure AD once the upgrade is complete, but i cannot connect or migrate anything with server essentials. (everything else i use the server for (sql, dns, group policy, hyper-v) will be unaffected when reviewing the 2022 feature list)

2) Only me and one other admin physically log into the server, however there are several other AD user accounts, whose files are stored on the server and are accessed via other workstations which are manage with group policy. Will I need CAL's for each user that has an active account on the server, regardless of if they actually use the server itself? Or only the two of us that actually access the server itself?

3) Are there any other licensing requirements and/or incompatibilities that i should be aware of doing an upgrade such as this? I really want to upgrade this server so that i can utilize Azure services but I do not want to do this upgrade, only to find out that my server is no longer usable.


The hardware is more than adequate, so no concerns there.


I realize that 2016 is out of service, and server essentials was kind of an oddball version of server so any guidance here would be greatly appreciated.

7 Replies
Also available in my licenses:
Windows Server 2022 Remote Desktop Services device connections (50) - 4 keys remaining
Windows Server 2022 Remote Desktop Services user connections (50) - 4 keys remaining

Would these act as the CAL's I need? 50 users/devices per license, so technically i have 200 licenses available?
best response confirmed by danleepre (Copper Contributor)

I'd suggest installing the hyper-v role (as only role) on host, then stand up two (or more) virtual machines for the various roles. The domain migration should not be a problem.


The two prerequisites to introducing the first 2019 or 2022 domain controller are that domain functional level needs to be 2008 or higher and older sysvol FRS replication needs to have been migrated to DFSR


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.

A Windows Server CAL is a license that grants access Windows Server. CALs are used in conjunction with Microsoft Windows Server OS licenses to allow Users and/or Devices to access and utilize the services of that windows server
- User CALs allow a single user access to Windows Server from an unlimited number of devices
- Device CALs allow an unlimited number of users to access Windows Server from a single device







Just checking if there's any progress of updates? Please don't forget to mark helpful replies.



Thank you, that is exactly everything that i needed to know. I was asking if i could do an in-place upgrade, but i have a fallback server that does not host mission critical resources, but is configured almost identically to the host that i do want to upgrade, so I am testing this upgrade process on that server now and if everything goes as planned, will be following this method on the primary host.

An in-place upgrade is a very risky move and not recommended. Plus, you'll end up with the domain controller on the hyper-v host which is also not recommended.



Okay, well it makes sense why i was struggling to find any solid information on in-place upgrades then.
Perhaps I should wait until i get an additional physical server capable of running my services to make the migration on my primary.

Sure thing. Another option is to migrate the domain controller to some temp box allowing you to rebuild the other machine in preparation.