Windows Default Upgrade Plan

12th December 2024

In-place Upgrade servers <2012r2 to 2022, Backup first, In-place isn’t ideal but it’s a known length of time which allows planning 1 server / weekend. Note; can’t upgrade using an EVAL windows .iso image.

Install 0patch on <win2012 servers that can’t be upgraded quickly ie a few per evening. Important for internet facing devices.

Replace Intel Gen7 CPU and older hardware gradually before the Win10 EoS

You CANNOT do an In-Place upgrade using a EVAL version of Windows and Keep Existing Files !!!!!!!!!

If you need to change from Std to Datacenter Edition, (due to your destination license key):

DISM.exe /Online /Get-CurrentEdition

DISM.exe /Online /Get-TargetEditions

I believe this only indicates if you can upgrade from ServerStandard to ServerDatacenter. and i don’t think windows can be down-graded

https://learn.microsoft.com/en-us/answers/questions/2187047/keep-personal-files-and-apps-option-greyed-out-whe

Show License type, make sure your purchased license and installed version match.

slmgr /dli (or slmgr /dlv)

Convert between retail, volume-licensed, and OEM licenses

slmgr.vbs /ipk <product key>

Need a NON-Eval version to do an In-Place Upgrade

Windows Server 2022 Eval version .iso 5,420,564kb

Windows Server 2019 Eval version .iso 5,172,572kb

You will likely NOT be able to upgrade an OEM version of windows. May be able to work-around this by giving the server a RETAIL product#.
DISM /online /Set-Edition:ServerStandard /ProductKey:N69G4-B89J2-4G8F4-WWYCC-J464C /AcceptEula

Retail Key Server 2016 Std $10 here (NOT TESTED, purchase at your own risk)

WINDOWS SERVER 2016 STANDARD $150 here

After copying the ISO files to a folder I ran the following:

md c:\mount

dism /mount-wim /wimfile:c:\ISO\sources\install.wim /mountdir:c:\mount /index:2

dism /image:c:\mount /get-currentedition

dism /image:c:\mount /get-targeteditions

dism /image:c:\mount /set-edition:ServerStandard

dism /unmount-wim /mountdir:c:\mount /commit

The author ran setup and it still listed eval under the options, but then it allowed me to choose to keep my files.

Error when tried on Server 2012r2:

C:>dism /image:c:\mount /get-currentedition
Deployment Image Servicing and Management tool
Version: 6.3.9600.19408
Error: 50
To service this Windows image requires the latest version of the DISM. See http:
//go.microsoft.com/fwlink/?LinkId=293395 to find the latest version of DISM,
and http://go.microsoft.com/fwlink/?LinkId=293394 to learn how to install the la
test version of DISM from the ADK on your computer.
The DISM log file can be found at C:\Windows\Logs\DISM\dism.log

C:>dism /image:c:\mount /get-targetedition
Deployment Image Servicing and Management tool
Version: 6.3.9600.19408
Error: 50
To service this Windows image requires the latest version of the DISM. See http:
//go.microsoft.com/fwlink/?LinkId=293395 to find the latest version of DISM,
and http://go.microsoft.com/fwlink/?LinkId=293394 to learn how to install the la
test version of DISM from the ADK on your computer.
The DISM log file can be found at C:\Windows\Logs\DISM\dism.log

And it doesn’t let me Keep Files & Folders

More info here