Migrating from Windows XP to Windows 8.1: Enterprise Computing

Microsoft will stop supporting Windows XP on April 8 — see our Windows XP End of Support Guide for more details — so now is the time to upgrade to Windows 8. In this article, I’ll look at Microsoft’s free enterprise tools for migrating multiple PCs to Windows 8, and point you to useful resources for starting your migration project.

Assessing Hardware for Windows 8 Readiness with the Microsoft Assessment and Planning (MAP) Toolkit

The Microsoft Assessment and Planning (MAP) Toolkit 9.0, which can be downloaded from Microsoft, collects information about processor architecture, RAM, and free disk space from Windows XP Professional PCs. MAP’s agentless architecture gathers data using Windows Management Instrumentation (WMI) and stores it in a SQL database, allowing administrators to generate reports to provide an overview of which PCs are Windows 8 ready.

Windows 8 requires 1GB of RAM (or 2GB for the 64-bit version), a minimum of 20GB free disk space and a DirectX 9 compatible graphics card with WDDM driver. Additionally, CPUs must support the following features:

  • Physical Address Extension (PAE)
  • NX processor bit (NX)
  • Streaming SIMD Extensions 2 (SSE2)

Fix Legacy Applications using the Application Compatibility Toolkit (ACT)

One of the primary showstoppers that has caused organizations to stay with XP is legacy applications that are not compatible with Windows 8 or Internet Explorer 11. Many of these applications cannot be updated because the developers either no longer support the application, went out of business, or if the application was created in-house, the developers may have left long ago.

The Application Compatibility Toolkit (ACT), which is part of the Windows Assessment and Deployment Kit (Windows ADK), provides administrators with the tools to check and fix compatibility problems with legacy applications. Compatibility shims can be distributed to overcome problems with User Account Control (UAC), or other issues associated with running legacy apps on modern versions of Windows. ACT also provides comprehensive inventories of applications used across PCs in your organization and identifies potential compatibility issues.

Windows XP end of support deadline
Windows XP end of support deadline

Hyper-V for Legacy Application Compatibility

Despite the compatibility fixes available for legacy applications, there are still some programs that refuse to run on newer versions of Windows and IE. In this situation, virtualization may be the only solution.

Windows 7 Professional, Ultimate and Enterprise editions included a feature called Windows XP Mode, which included a licensed copy of Windows XP running in Microsoft’s Windows Virtual PC. XP Mode provided tight integration with users’ desktops, such as the ability to run apps in the VM on the host’s desktop, and launch those apps from the host’s Start menu.

Windows XP Mode is not available for Windows 8, nor is support for Windows Virtual PC. But Windows 8 includes Hyper-V out of the box, so if you still have licensed copies of Windows XP, it is possible to run it in a sandboxed virtual environment. For more information on how to work with Hyper-V in Windows 8, see the Windows 8 Client Hyper-V five-part series on Petri.

Much of Windows XP Mode’s integration can be replicated with client Hyper-V, including the ability to run apps installed on the guest VM in windows on the host’s desktop. For more information on enabling this functionality, see Enable RemoteApp Capability in Windows XP SP3 on Petri.

Migrating to Windows 8 with the Microsoft Deployment Toolkit (MDT)

There are several ways to deploy Windows 8 using the Microsoft Deployment Toolkit. If you don’t have System Center Configuration Manager (SCCM) in place, you can use MDT to manually deploy custom Windows 8 images, or use Light Touch Installation (LTI), which requires minimal user input.

Your custom Windows 8 images can be stored on a deployment share, or you can use Windows Deployment Services (WDS) to distribute images to PXE Boot-enabled computers. If you don’t have WDS and PXE Boot-enabled network adapters on your PCs, you can boot from a USB stick containing a customized Windows PE (Preinstallation Environment) image that will connect PCs to your deployment share.

For more information on using the Microsoft Deployment Toolkit to install Windows 8, see “Windows 8 Deployment Using MDT 2012: Setup and Configuration” on Petri. Additional information on updating existing Windows 8 images, migrating to Windows 8.1 Update and the new servicing baseline included in the update that will be required to patch Windows starting May 2014, can be found at Microsoft’s website.

Preserving User Profiles and Personal Files with USMT

From a technical point of view, it’s not possible to upgrade XP to Windows 8. You can run the Windows 8 installer in XP and you will be prompted to upgrade, but what this really does is copy the local user profiles, install Windows 8 on the PC, and then reinstate the user profiles and personal files in the new OS.

In an enterprise environment, the recommended way to reinstate user profiles and files on a PC after Windows 8 has been installed is to use the User State Migration Tool (USMT). The tool can be used standalone, to scan multiple PCs and store user state data in a centralized location ready for redeployment to a new or upgraded PC, or as part of an MDT task sequence. When the USMT plugin is enabled in an MDT task sequence, it will give the option to migrate existing user profiles and files to Windows 8 as part of the LTI process.


Microsoft recommends using the Key Management Service (KMS) to activate Windows. After Windows 8 has installed and established connectivity to KMS, it will be automatically activated, saving you from having to manage keys during the build process and eliminating another element that can potentially go wrong during setup. KMS can only be used with Enterprise editions of Windows 8.

Migration Complexity

In some cases, large organizations have been slow to move away from Windows XP – and who can blame them, considering the complexities and costs involved in migrating to a new operating system, a task only compounded by the presence of legacy applications.

Despite the security risks of staying with Windows XP after the April 8 cutoff date, there are still some CEOs who are not planning to move off XP anytime soon, or are holding out for Windows 9. But Windows 8 has enough security, reliability, manageability, and performance improvements to make it a worthwhile investment, so take the opportunity to maintain security and reduce support costs in the long-term by ditching Windows XP as soon as possible.