For when you want to let go, but can’t completely.

Mitch, I have been using my Windows 7 laptop for nearly three years.  It has all of my applications on it, and because of the custom dev work that I do a lot of what I have in there simply cannot be recreated – anywhere, let alone on another OS.  I want to upgrade my primary laptop to Windows 8, but cannot afford to lose my customizations and my environment.  What can I do?

I got this question from a peer last week and feel his pain; so many people have customized their desktop environment in ways that (they feel) is a stop-wall to upgrading – either in-place or on new hardware.  Fortunately Microsoft has some great tools that will help you out.

Hyper-V is now included in the Windows 8 desktop client.  You can capture your Windows 7 desktop image to a Virtual Hard Drive (VHD) and then create a new VM on your Windows 8 client and attach it.  But how can you capture that image?


Microsoft has a free set of tools called the Sysinternals Suite.  One of those tools is called Disk2vhd.  Download it to your Windows 7 machine and run it – it will transfer your entire hard drive (or drives) to VHD files.  It is agentless and does not require an install – just run it and you can immediately convert every attached volume.

This method will actually work with any supported version of Windows.  That is not to say that it will not work with Windows NT 3.51, but it is not supported and I certainly have not tested it.  So if you want to keep your Windows XP installation as a crutch (you have 307 days left remember!) you can use the same methodology with that OS too.

Of course, when you boot to the VM you may have some issues because the hardware set is completely different.  In newer operating systems you may have to download some of the drivers for it to work properly; for legacy (Windows XP and earlier) OSes you may have to do a full install-in-place; do this carefully because depending on your media your apps may or may not continue to work (do NOT try to use OEM or Upgrade media for this!).

For bonus points, if you have a full Windows Server 2012 system up and running you can create the VM as a VM on that host, and let your Windows 8 use all of its RAM.  However with the amount of RAM in computers these days, coupled with the incredible memory management and compression with Hyper-V, you should be okay.

Questions?  Feel free to ask… and have a great day!


4 responses to “For when you want to let go, but can’t completely.”

  1. Nice article. It can also be used by those reluctant to upgrade to Win8 because they do not have the confidence that all their programs will work on Win8.

  2. A clarification over the OEM/Upgrade media issue:

    A OEM installed OS (typical in most laptop purchases) by license can’t be installed on different hardware (some exceptions with regards to repairs). You will be required to change the Product Key for the VM instance away from the OEM SKU to for a product SKU that you (in addition) legally own. A MSDN or TechNet subscription can definitely come in handy in these circumstances, but note that these offerings also set restrictions regarding usage/purpose of the OS installation.

    Your reference to “Upgrade” media has similar considerations with regards to licensing, since it is permanently tied to the OS license/SKU/Product Key that it was used to upgrade(and it typically that is an OEM SKU).

    Notwithstanding these licensing caveats, OEM and vendor specific Upgrade media, as you mention, is, generally, very hardware specific and usually will not install successfully on “foreign” hardware.

    Off-the-shelf, “Full-Package-Product” (FPP), which can be use as “upgrade” media, is a SKU which can be moved (not copied) from device to device.

    *** So the question arises: if you are migrating an image of OEM licensed OS away from failing hardware and onto, say, a virtualized system, would that be seen as an acceptable reuse of the OEM license? ***

    Hint: Typically I upgrade my laptop’s OS with a MSDN/TechNet version since the OEM versions typically are “Home”, limited feature set, SKU’s. To aid installing a new OS, I do usually copy over the “%windir%\System32\DriverStore\” of the active OEM installation onto a USB stick so as to resolve “unknown” device issues (use the scan folder option in updating these under device manager). Subsequent Windows Update may upgrade these, but it usually goes over easier once they are “known” devices requiring, perhaps, an upgrade.

    1. A lot of good points… I replied in an article for you!

  3. […] this week I wrote a piece called “For when you want to let go… but can’t completely.’  I got a few interesting responses to it, but one really well thought out one from H. […]

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