2016 WSE to 2019 or 2022 as in-place upgrade


I have WSE 2016 and I’m looking for a way to go to 2019 or 2022 while keeping all the client computer backup database history intact. The history has backups from previously decommissioned computers that I still need to keep and be able to mount images of those from the backup restore process if needed.

In addition, the client computer backup system needs to continue the backup scheduling on the current computers into the backup database; and be able to do bare metal restores.

My WSE 2016 has Windows ADK installed. This server has many programs and settings that I don’t want to redo (I don’t even remember how I did all the things I did in IIS for local services I’m using). So, I need an in-place upgrade that will handle migrating all the users, computers, applications and roles in an automated way, and give me a list of the things that it wasn’t able to automatically handle.

What I’m looking for is a script that I can run on my existing WSE 2016 that will extract all the relevant WSE cabs, files and registry settings from the currently running WSE 2016 and insert them into a WIM from an official Server 2019 or 2022 ISO to create a new ISO (and autounattend.xml if needed for post migration steps that may be custom to implementing WSE) that will allow an in-place upgrade to 2019 or 2022 with WSE already enabled. I would then image my server into a VMs (it would be a very large VM) and clone three existing VMs (one win7, one win81 and one win10) and then do the in-place upgrade on a virtual Lan segment to make sure it is all working right.

I’m also worried that your WSEE Installer might have modified cabs or other binary files. This is why I’m asking for a script that handles creating a modified WIM that doesn’t rely on modified cabs or binaries that are not verifiably generate from official sources. If modification of any existing cab is needed to make it work, the script has to take the original cab from my server or an official MS ISO, make the modifications that are necessary, and resign it locally if that is needed. I realize this is asking a lot. I am willing to sign an NDA. Is the above possible?

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Best Answer

Yes, you sure are asking for quite a lot there. :- O

About all I can tell you there is that you can indeed in place upgrade Windows Server 2016 to Windows Server 2019/2022 seeing as Microsoft fully supports doing that. If you are starting with the Windows Server 2016 Essentials SKU (as opposed to Windows Server 2016 Standard/Datacenter with the WSEE server role added), then you will need to in place upgrade to the (horrible) Windows Server 2019 Essentials SKU first, and then transition it into Windows Server 2019 Standard. From there, you can stay with Windows Server 2019 Standard, or you can further in place upgrade it to Windows Server 2022 Standard if so desired. Regardless of the route that you take, Microsoft will forcefully remove all traces of the WSEE server role from the upgraded server (by their design). The WSEE Installer can then be used to (properly and securely) add back all of the required “Essentials bits” to the server. All of your existing Essentials users, connected devices, settings, backups, etc. will remain in tact during the in place upgrade(s). For further info you can read my comments about performing an in place upgrade over here.

That’s about the best you’re going to find, and I’m positive that no one else can offer you anything better (unless you have a whole lotta money to throw at the project that is).

Best of luck.

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My system was originally installed using this method: https://learn.microsoft.com/en-us/windows-server-essentials/install/customize-and-deploy-windows-server-essentials

This uses the WSE 2016 SKU and creates a Hyper-V host install without WSE and WSE VM. All in a single install and using a single license key. I also own separate licensed to Server 2016 Standard, as well as 2019 and 2022 Standard (and all previous Server version back to 2003) through long term subscription to MSDN Microsoft Partner Program. This makes it simple to export the VM to test upgrade scenarios.

I read your comments at the link you provided regarding 2019 forcefully removing WSE during an in-place upgrade. I’ve used ADK with Windows 7 and 10 so far. And with my prior use of DISM to create the customized WSE 2016 server install, I’m wondering why those tools (ADK and DISM) can’t be used to modify a 2019 Server’s ISO to remove the uninstallation steps, and/or mitigate them by apply the registry entries, enabling roles, and running the scripts necessary to reimplement WSE during an in-place upgrade.

Also, on a side note (I don’t need a reply to this paragraph as it’s probably a settled matter): But I don’t understand the logic behind thinking that there is some copyright issue in providing a WSE installer, if the installer extracts the relevant registry entries, scripts and packages from a running and licensed WSE 2016 (or ISO) and applies them to a 2019 Standard ISO using ADK/DISM. It’s been well established (at least in the US) that content shifting is not a copyright issue. But I do accept that you should be compensated for your know-how in some way. However, although I may buy WSE RemoteApp or WSE WorkFolders in order to get the installer, I have no need for them and until a point in time that I do, I do not want any custom binaries for those features running on the upgraded server.

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Feel free to try using the ADK, DISM, etc. to add the Essentials bits from 2016 to 2019. I attempted doing just that in the early days when I was first working all of this stuff out and it didn’t pan out too well for me back then (don’t recall exactly why now seeing as it’s been way too many years since I first attempted doing so). That being said… I think that Microsoft will still forcefully remove all of the Essentials bits from the server even if you were successful at recreating an ISO with the WSEE server role seeing as that behavior is simply hard coded into the Windows Server installer I believe (unless it’s a package that you can identify and remove from it that is). Personally, I didn’t want to spend any more of my time and resources chasing rabbits down their holes and so I took a completely different (and arguably much more difficult) approach instead.

Besides that, there are many challenges that still need to be overcome when attempting to use WSEE (successfully and securely) on newer versions of Windows Server (seeing as Microsoft only designed it to run on 2016) that can’t be overcome by simply dumping its assemblies, etc. onto a newer version of Windows Server. Thus, it was just better in the long run for me to build the WSEE Installer instead (which has nearly five years of my experiences wrapped up into it now). Lastly, how are you going to keep it automatically updated (and secure) down the road for the folks using it, and how are you going to be able to support doing in place upgrades to newer releases of Windows Server when doing it that way??? The WSEE Installer/WSEE Updater packages that I’ve built handle doing all of that for folks natively now. They just work, and work really well.

As for the copyright stuff… I’m not a Microsoft license specialist nor a copyright attorney and so I don’t even want to attempt to decipher what’s allowed and what’s not when it comes to copyright law. I’d rather just leave that to the lawyers and go on the simple assumption that everything infringes on Microsoft’s copyrights and so you have to proceed “at your own risk” when attempting any of this kind of stuff. If folks aren’t okay with that, then they should simply stick with using 2016 Essentials until Microsoft stops supporting it on January 12, 2027 (as it still works great anyway).

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