Most medium to large size enterprises are on top of Windows Server operating system upgrades. In my experience, infrastructure teams don’t tend to keep unsupported operating systems in their managed environments unless it is necessary. Most server teams will update their domain controllers when a version of Windows Server has been deemed stable. Other servers managed by the infrastructure teams can be upgraded as application vendors begin to support (or even require) newer Windows Server operating systems.
Fortunately, most applications that require backends to be set up and maintained by in-house infrastructure teams are more likely to be kept up to date than their desktop counterparts. Client-side applications typically run on desktops and can often be left in version and support limbo with administrators expected to work miracles to keep them functioning on modern Windows desktop operating systems, regardless of whether the vendor supports the OS.
One solution End User Computing teams have turned to for those tricky client-side applications that won’t work on Windows 10 or Windows 11 has been to install and run the applications on published desktops that use a Windows server operating system as the base OS.
Real-World Example
In a previous Windows 7 to Windows 10 migration project, my team ran into an application that threw an error when opening certain menus that called built-in windows dialogs. These worked fine on Windows 7 but no longer worked on Windows 10. As the migration project was left late in the Windows 7 lifecycle, a decision was made to simply hold off on migrating the users of that application until the end of the project. We would then figure out what to do when our Windows 7 footprint was smaller.
The quickest solution and path of least resistance was chosen when we re-visited that application. The application was tested on Windows Server 2012 R2, where we found it did in fact work on that OS. Hosting that application on those Windows Server-based machines allowed us to complete our migration project without further delay. Since end of life for Windows Server 2012 R2 was years out, dealing with this application was a low priority for the organization.
Support for Windows Server 2012 R2 Ends October 10, 2023
Fast forward to today. Windows Server 2012 R2 is about to enter extended support. Paying for extended support can be costly. Suddenly those legacy applications some of us deferred finding permanent solutions for are starting to rear their ugly head once more. If you had a similar scenario to the one I detailed above but on Windows Server 2008 R2 your situation is even more dire. Extended support for on-premises instances of Server 2008 R2 has now ended. Extended support for those hosting Server 2008 R2 in Azure has less than 12 months left.
How to Bring Your Apps to a Modern OS
Fortunately, there is a solution to bring those applications forward. You can put those legacy applications in Cloudpaging containers to lift and shift them to any modern Windows OS. While you may have turned to Windows Server operating systems in the past out of necessity, you can now package those applications into Cloudpaging containers and dynamically provision them to Windows 10 or Windows 11 desktops (like you would have done in the first place, had the applications worked).
Alternatively, if you parked some legacy applications on Windows Server 2012 R2 machines due to compatibility issues on Windows Server 2019 or 2022, you can try to containerize those applications with Cloudpaging and deliver them to your modern Windows Server operating system of choice.
Conclusion
If applications are holding you back from eliminating legacy Windows Server operating systems in your organization, you owe it to yourself to try out our application containers to progress your modernization efforts. You gain a solution to accelerate your current modernization efforts and solve for future application compatibility issues. With the security risks of running unpatched systems more precarious than ever, you cannot afford to fall outside of Microsoft’s support. For more detailed information on how we can help migrate legacy applications, please check out our previous blog post here.