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Windows Server Upgrade Path

Microsoft has a simple step-by-step guidance for modernizing Windows Server. Please refer the link:  https://www.microsoft.com/upgradecenter


In this article a table has been prepared based on Microsoft's guide. 

    

Product

Server 2008 R2 SP1

Server 2012

Server 2012 R2

Server 2016

Server 2019

1

Windows Server 2008 R2

Direct

Direct

Direct

Yes

Yes

2

Windows Server 2008 R2 SP1

-

Direct

Direct

Yes

Yes

3

Windows Server 2012

X

-

Direct

Direct

Yes

4

Windows Server 2012 R2

X

X

-

Direct

Yes

5

Windows Server 2016

X

X

X

-

Direct

7

Windows Server 2019

X

X

X

X

-

Direct - Can be upgraded directly with one setup

Yes - Can be upgraded by consecutive upgrade processes

Note

During OS version upgrade, the OS edition must remain same or can be upgraded. The edition can not be downgraded by in-place installation. Example: Windows Server 2008 R2 SP1 Standard can upgrade to Windows Server 2012 Standard or Datacenter edition.

Upgrade path from Windows Server 2008 is not tested by Ginesys Team. You may contact your server administrator for this. A reference blog link is mentioned in Reference section.


References:

  1. https://www.microsoft.com/upgradecenter
  2. https://www.thomasmaurer.ch/2011/02/in-place-upgrade-windows-server-2008-to-windows-server-2008-r2/