Hyper-V: Upgrade to Windows Server 2008 R2 from Windows Server 2008 with Hyper-V

In the following post I will describe three methods for upgrading from Windows Server R2 from Windows Server 2008 with Hyper-V. The methods described here are covered in MS Support KB 957256. After listing the methods I will describe why I prefer one of the methods.


Before you upgrade.


The upgrade process is not complex however you need to be careful. An important first step is to bring all of your virtual machines into a single state. You should review each virtual machine and establish a clean VM to be migrated. This VM must be in a shut down state. Your snapshots leading up to the current state must be merged since snapshots are not fully compatible.


Method 1


Perform an in-place upgrade of the parent partition from Windows Server 2008 to Windows Server 2008 R2.

Note During the upgrade, the compatibility report will inform you that you must remove the Hyper-V role by using Server Manager before you continue with the upgrade. This is not necessary. However, before you continue with the upgrade, note the following:


  • All virtual machines must be shut down before the upgrade. The Saved States feature is incompatible between Windows Server 2008 and Windows Server 2008 R2. If the parent partition is upgraded with any virtual machines in a saved state, you must right-click the virtual machine, and then click Discard saved state to turn on the virtual machine.
  • Because the Snapshot functionality uses the Saved States feature, Snapshots are not fully compatible between Windows Server 2008 and Windows Server 2008 R2. Virtual machines will start successfully to the snapshot that was applied when the virtual machine was shut down before the upgrade. This is denoted in Hyper-V Manager by the green arrow under the snapshot that points to Now.

    To turn on the virtual machine with any other snapshot, follow these steps:

    Note The following steps assume that you have to continue using all snapshots configured for the virtual machine. If you no longer require snapshots, you can delete your snapshots by using Hyper-V Manager, and then shut down the virtual machine for the data to merge with the parent virtual hard disk.
    1. Using Hyper- V Manager, right-click the snapshot that you want to apply, and then click Take Snapshot and Apply. This action will take a new snapshot from the currently applied snapshot. This new snapshot will now be compatible with Windows Server 2008 R2. If you select this option, any changes that you may have made to the state of the virtual machine since the last start will be saved.
    2. After the new snapshot is taken, the virtual machine will go into a saved state. Right-click the virtual machine, and then click Delete saved state.
    3. Turn on the virtual machine.
    4. When the virtual machine has started, repeat these steps until there is a single snapshot remaining.
    5. When you have reached the last snapshot, take a new snapshot to capture the current state of the virtual machine to have a Windows Server 2008 R2-compatible snapshot.
  • After the upgrade, update the Integration Services. To do this, open the Virtual Machine Connection window, and then click Insert Integration Services Setup Disk on the Action menu.

    Note On a Windows Server 2008 R2-based computer, the Integration Services for Windows Vista and Windows Server 2008 will be listed in Programs and Features as “KB955484″.

Method 2


Migrate to another server: Export a virtual machine from a Windows Server 2008 server that has Hyper-V enabled, and then import it to a server that has Windows Server 2008 R2 with Hyper-V enabled.

Note The virtual machine must be shut down before you export it. If you exported the virtual machine with a saved state, you cannot restore the virtual machine on Windows Server 2008 R2. To start the virtual machine after you import it to Windows Server 2008 R2, you must discard the saved state before you can turn on the virtual machine.

If the virtual machine has snapshots, these snapshots must be merged before the export or you must use the steps from Method 1 to recover and re-create the snapshots.

After you import the virtual machine, update the Integration Services. To do this, open the Virtual Machine Connection window, and then click Insert Integration Services Setup Disk on the Action menu.

Note On a Windows Server 2008 R2-based computer, the Integration Services for Windows Vista and Windows Server 2008 will be listed in Programs and Features as “KB955484″.


Method 3


Backup and Restore to new server: To use backup software that uses the Hyper-V VSS Writer, back up a virtual machine that is running on Windows Server 2008, and then restore it to Windows Server 2008 R2.

After you restore the virtual machine, update the Integration Services. To do this, open the Virtual Machine Connection window, and then click Insert Integration Services Setup Disk on the Action menu.

Note On a Windows Server 2008 R2-based computer, the Integration Services for Windows Vista and Windows Server 2008 will be listed in Programs and Features as “KB955484″. 


My Preference


Although Method 3 might take the longest it provides a number of safe guards. 


  1. It ensures you have a proper backup strategy.
  2. It tests your backup strategy with little or no consequense.
  3. You have a fall back position to the original server which is not altered during the process.
  4. It simplifies the process of cleaning up the snapshots since the backup sees only one consistent state of the VM.
  5. In any other of the three methods you should have a complete back up.

Jeff Loucks
Available Technology
Available Technology

4 thoughts on “Hyper-V: Upgrade to Windows Server 2008 R2 from Windows Server 2008 with Hyper-V”

  1. I wish Microsoft would somehow automate the “Insert Integration Services” updating that is required when going to R2. It’s a pain the way it is now – I have dozens of VMs.

  2. I have tried Method 1 and everything seems to work. But one thing is bothering me.  After creating a new snapshot and deleting the snapshot, the hierarchy of the snapshots is all messed up.  All the children snapshots are at the parent level.  Is there no way to preserve the hierarchy?

  3. Ben, you have to pay attention to details. I give the value of experience in this article which I think is the best practice. If you look at the other comments you will note that people have been unsuccessful using the other methods. Not because those methods do not work but because people do not take in to account the effect of not doing the compatibility steps. Essentially, the difference in this post is the value of experience and dilligience. With expereince going through this process you will find that a good backup to recover from lost VMs, Config Files or Hyper-V inability to resolve the Simlinks in certain scenarios is very valuable. If you add in that proper documentation is not as common as it should be, administrators should be diligent in not following Method 3. And of course you always need a good backup.
    Jeff Loucks

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