Upgrading Windows Server 2008

Solution 1:

It looks like you can, provided you're on Web R2, or can upgrade to Standard R2.

Supported upgrade paths

The table below shows which Windows operating systems can be upgraded to which editions of this release of Windows Server 2008 R2.

Note the following general guidelines for supported paths:

  • In-place upgrades from 32-bit to 64-bit architectures are not supported. All editions of Windows Server 2008 R2 are 64-bit only.
  • In-place upgrades from one language to another are not supported.
  • In-place upgrades from one build type (fre to chk, for example) are not supported.
  • If you do not see your current version in the left column, upgrade to this release of Windows Server 2008 R2 is not supported.

If you are running: You can upgrade to this edition:

Windows Server 2003 Standard Edition with Service Pack 2 (SP2) or Windows Server 2003 R2 Standard Edition Windows Server 2008 R2 Standard, Windows Server 2008 R2 Enterprise

Windows Server 2003 Enterprise Edition with SP2 or Windows Server 2003 R2 Enterprise Edition Windows Server 2008 R2 Enterprise, Windows Server 2008 R2 Datacenter

Windows Server 2003 Datacenter Edition with SP2 or Windows Server 2003 R2 Datacenter Edition Windows Server 2008 R2 Datacenter

Server Core installation of Windows Server 2008 Standard with or without SP2 Server Core installation of either Windows Server 2008 R2 Standard or Windows Server 2008 R2 Enterprise

Server Core installation of Windows Server 2008 Enterprise with or without SP2 Server Core installation of either Windows Server 2008 R2 Enterprise or Windows Server 2008 R2 Datacenter

Server Core installation of Windows Server 2008 Datacenter Server Core installation of Windows Server 2008 R2 Datacenter

Server Core installation of Windows Web Server 2008 with or without SP2 Server Core installation of either Windows Server 2008 R2 Standard or Windows Web Server 2008 R2

Full installation of Windows Server 2008 Standard with or without SP2 Full installation of either Windows Server 2008 R2 Standard or Windows Server 2008 R2 Enterprise

Full installation of Windows Server 2008 Enterprise with or without SP2 Full installation of either Windows Server 2008 R2 Enterprise or Windows Server 2008 R2 Datacenter

Full installation of Windows Server 2008 Datacenter with or without SP2 Full installation of either Windows Server 2008 R2 Datacenter

Full installation of Windows Web Server 2008 with or without SP2 Full installation of either Windows Server 2008 R2 Standard or Windows Web Server 2008 R2

Server Core installation of Windows Server 2008 R2 Standard Server Core installation of either Windows Server 2008 R2 Standard (repair in place) or Windows Server 2008 R2 Enterprise

Server Core installation of Windows Server 2008 R2 Enterprise Server Core installation of either Windows Server 2008 R2 Enterprise (repair in place) or Windows Server 2008 R2 Datacenter

Server Core installation of Windows Server 2008 R2 Datacenter Server Core installation of either Windows Server 2008 R2 Datacenter (repair in place)

Server Core installation of Windows Web Server 2008 R2 Server Core installation of either Windows Web Server 2008 R2 (repair in place) or Windows Server 2008 R2 Standard

Full installation of Windows Server 2008 R2 Standard Full installation of either Windows Server 2008 R2 Standard (repair in place) or Windows Server 2008 R2 Enterprise

Full installation of Windows Server 2008 R2 Enterprise Full installation of either Windows Server 2008 R2 Enterprise (repair in place) or Windows Server 2008 R2 Datacenter

Full installation of Windows Server 2008 R2 Datacenter Full installation of either Windows Server 2008 R2 Datacenter (repair in place)

Full installation of Windows Web Server 2008 R2 Full installation of either Windows Web Server 2008 R2 (repair in place) or Windows Server 2008 R2 Standard