[Root] Access is an advice column for IT professionals.
How Do I Secure Business Apps That Need Prehistoric Versions of Windows?How Do I Secure Business Apps That Need Prehistoric Versions of Windows?How Do I Secure Business Apps That Need Prehistoric Versions of Windows?
A Windows admin seeks advice on managing critical legacy applications that rely on unsupported operating systems like Windows Server 2008. Here are four tips to help protect these outdated systems.
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Dear [Root] Access,
I'm a Windows administrator for a medium-sized company. We have critical business applications that need older versions of Windows to function. In some instances, it's Windows Server 2008; in one case, it's even Windows XP . These apps are "mission critical," meaning we can't simply replace or upgrade them without disrupting operations.
I know the security risks of running unsupported operating systems, but my bosses want to delay an overhaul.
I've implemented some basic protections, like isolating these systems from the broader network and limiting user access. I don't know if that's enough or if there are better strategies I'm overlooking.
Since these systems are no longer supported, I can't rely on Microsoft's regular patches. Are there safe ways to address vulnerabilities, or am I stuck crossing my fingers and hoping nothing goes wrong?
—Living in the Past
Dear Living in the Past,
Even large enterprises sometimes have badly outdated mission-critical applications that they continue to run. In fact, I know of a major retailer that still runs its point-of-sale systems on Windows 2000. So, you are not alone in this.
Related:I’m Struggling to Update My Hybrid IT Environment—Can Powershell Help?
Even if you can't patch your legacy application and replacing it is not an option, you can still take some steps. The basic protections you have implemented are a good start, but you might also consider the following four measures.
1. Upgrade Your OS and Use Compatibility Mode
The first to consider is whether upgrading the underlying operating systems is possible. A more secure OS will go a long way toward improving your application's security. While you've mentioned that these applications run on Windows Server 2008 and Windows XP, you might be able to take advantage of the Windows application compatibility feature. Newer versions of Windows can partially emulate legacy environments on a per-application basis. For example, Compatibility Mode can force an application to run in reduced color mode, emulate a 640x480 screen resolution, or run with local administrative permissions.
2. Migrate Legacy Apps to a VM
If running the application on a new OS isn't an option, migrating it to a virtual machine could be a viable alternative. While this won't fully resolve security concerns, it may offer improvements by placing the application on modern infrastructure. At the very least, virtualization protects against hardware failure. This is important since any server still running Windows Server 2008 is likely running on extremely old hardware that could fail at any time.
Related:How Technical Debt Can Impact Innovation and How to Fix It
3. Update Application Dependencies
You may also find you can patch certain parts of the application, even if a complete upgrade isn't possible. Many applications rely on external dependencies . Even if the application vendor no longer supports the application itself, its dependencies might have newer versions available.
For example, a more recent version may be available if your application depends on a C++ redistributable. While this wouldn't bring the entire application up to date, it could help address some unpatched vulnerabilities and improve security.
4. Check for Community Support
Another option is to check if the application has become community-supported. When an application vendor abandons a popular product, the community sometimes steps in to maintain it for users who still rely on it. In fact, one of the mission-critical applications I use has been community-supported for several years.
Sometimes, the community may not have access to an application's source code, so they will rewrite it themselves. This can sometimes lead to introducing new versions or even new features. While this practice is widespread with old PC video games, I have also seen it occasionally happen with business software.
Related:Where Did My Windows Server's Disk Space Disappear To?
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About the Author
Technology Analyst
Brien Posey is a bestselling technology author, a speaker, and a 20X Microsoft MVP. In addition to his ongoing work in IT, Posey has spent the last several years training as a commercial astronaut candidate in preparation to fly on a mission to study polar mesospheric clouds from space.
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