I am trying to do an in-place upgrade from Windows 2008 Standard (Sp2, 64 bit) to Windows 2008 R2 Standard.

The problem is that after running the setup executable, the wizard doesn't even mention the possibility of an upgrade. It somehow skips that step and jumps directly to the point where I can only choose the partition for a clean install. But using the same installation media on another Windows 2008 Sp2 server, the upgrade option is being shown without issues.

Can anyone help me with this? Thanks.

Short description of the server on which I am encountering this issue:

  • HP ProLiant DL380 G6 with Intel Xeon E5520 @2.27ghz
  • 53 GB free space on the OS partition
  • server roles: appication server, file services, hyper-v, web server (the server is mainly being used as a host for several Hyper-V VMs)
  • You might double check all the limitations on the upgrade path: technet.microsoft.com/en-us/library/dd979563(v=ws.10).aspx – Todd Wilcox Jun 29 '16 at 15:08
  • I did check the compatibility requirements and everything should be in order. Even if it wasn't, it wouldn't explain why the setup simply skips that step where I can select between "Custom Install" or "Upgrade". It just goes directly to the clean install step. – NuckT Jul 8 '16 at 14:00

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