Today I was facing a problem, when I tried to upgrade our one 2008 Standard server to Enterprise with the installation disk, it shows the current installed windows version is more recent.

So I googled a while and found this excellent post:

It shows simply use dism I can get the upgrade going:

So run the dism command under windows deployment tools command line:


dism /online /get-currentedition
dism /online /get-targeteditions
dism /online /Set-Edition:ServerEnterprise /ProductKey:12345-12345-12345-12345-12345


Then I was running into another problem, I dont have a product key, because the disk has the key and we use KMS from another server to activate it. So I have to get the key from an existing 2008 Ent server by the help of this post:

By the code of following VBS:

Set WshShell = CreateObject("WScript.Shell")
MsgBox ConvertToKey(WshShell.RegRead("HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\DigitalProductId"))

Function ConvertToKey(Key)
Const KeyOffset = 52
i = 28
Cur = 0
x = 14
Cur = Cur * 256
Cur = Key(x + KeyOffset) + Cur
Key(x + KeyOffset) = (Cur \ 24) And 255
Cur = Cur Mod 24
x = x -1
Loop While x >= 0
i = i -1
KeyOutput = Mid(Chars, Cur + 1, 1) & KeyOutput
If (((29 - i) Mod 6) = 0) And (i <> -1) Then
i = i -1
KeyOutput = "-" & KeyOutput
End If
Loop While i >= 0
ConvertToKey = KeyOutput
End Function


And I got the cdkey from the existing Enterprise 2008, use that key and command, I easily got the windows 2008 upgraded, it is actually faster! 


About Lei

I am an IT specialist with over 10 year experience - years on Automation, on-Premise or Azure.

I am happy to develop however never want be a full time developer. Only do what I have to do. If it has to be PowerShell,HTML, PHP, CSS, C#, VBS or JS, front end or backend, so be it, doesn't matter!

Spent years with Windows, SCCM, SharePoint, SQL and Exchange servers. For last several years, I have been actively working under On Premise > Azure environment.


Current Certificates:
    Microsoft® Certified-
  • -Enterprise Administrator
  • -Database Administrator
  • -SharePoint Administrator
  • -Administering and Deploying SCCM 2012
Red Hat Certified Technician
ITIL V3 Foundation - Practitioner

Working on Azure Certificates now and hopefully they can stop upgrading their questions one day! GIVE ME A BREAK!

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