Windows Server 2008 End of Life: Late and Down the Rabbit Hole?

Peter Carey

If you’ve been searching and reading articles on Windows Server 2008, you know you’re late to the show. For those of you running Windows Server operating systems, January 14, 2020 brought an end of support for Windows Server 2008. What does that mean for companies still running this version?

The good news is that the operating system will still run. There is no kill switch that Microsoft will trigger to shut down this operating system. The bad news, unfortunately, is that companies using Windows 2008 can no longer access security patches. This opens your business up to potential interruptions, caused by hackers, malware, and even end users. Ransomware attacks saw a 41% increase from 2018-2019 and will cost a breached company an average of $84,116. Do not leave yourself vulnerable to these bad actors. The end of support also impacts companies who need to meet certain compliance and regulatory standards. Failing to meet these can result in penalties, fines, and loss of client’s trust.

Now that this date has passed, what options are available? Three possibilities come to mind.


This involves migrating workloads to new location, such as Microsoft Azure. Moving to Azure allows you to postpone the upgrade. But ask yourself, do you really need to delay this again? The longer you wait, the less secure your data becomes.

Refactor or Re-architect

Refactoring is the advanced process of extracting the underlying functions of the application and re-architecting them for a dramatically different platform. This platform might include a server container and even azure data services.


This option leaves the workloads running in their existing environment, typically on premises. It involves upgrading to Windows Server 2016 or 2019.  While this option seems straight forward, proper planning and testing are required. You need to ensure your servers meet the minimum requirements to run the new operating system.

Moving Forward

Between these three options, refactor or re-architecting should be your least likely path.  While in theory this is still an option, it is one more likely to be discussed prior to the end of support date, because of the amount of time and effort needed. The time it takes to execute will leave you vulnerable longer and you won’t see the benefits until much later.

Your focus now is to avoid any further delays and move away from an unsupported operating system. Don’t leave your data at risk of breach or malware. But how do you decide on your best options? How do you develop a migration? Lastly, and more importantly, how to you keep workloads operating during migration? To guide you through this process, we’ve created a white paper that explains everything!

Peter Carey is a Senior Systems Engineer at Connection, and has over 20 years of experience in virtualization, storage, and hyper-converged infrastructure. He also carries VMware Certified Professional 6.5 certification. In his free time, Peter enjoys traveling and hiking.