Windows Server 2008 end-of-life: Fail to prepare, prepare to pay

14th January 2020 marked the official end date of the end-of-support lifecycle for Windows Server 2008, meaning organisations still utilising the product were left to run the risk of maintaining vulnerable systems that could prove crippling to business critical operations unless action was taken

For those companies unable to move applications to Microsoft Azure or shift to a new system, whether due to a lack of compatible applications or supporting technology and expertise, the only option proved to be the avenue of continuing to pay Microsoft for extended security updates (ESUs).

While ESUs so far have proven beneficial in ensuring that regulatory or compliance standards can continue to be met, while providing basic security bug fixes, it’s an expensive route to take, with costs continuing to rise as Microsoft largely moves resources away from supporting Windows Server 2008. As a result, businesses were understandably exploring alternative methods to securing their business following the first ESU payment in early 2020. The onset of the Covid-19 pandemic however left businesses needing to shift focus onto more urgent tasks, such as supporting their remote working employees. Now, with restrictions easing and businesses able to work towards pre-pandemic normality once again, preparing for the avoidance of another expensive ESU payment needs to be at the top of the business agenda.

The ESU countdown is entering the home straight

With the next ESU renewal set to take place in January 2022, the countdown is on for businesses. It means that with less than six months left until cost increases of 30%-50% are incurred, now is the time for action. The urgency to make a significant system change is further exacerbated by the fact that ESUs for Windows Server 2008 will come to an end in January 2023, with those systems then left exposed to dangerous security breaches.

In addition to increased costs, the other drawback with ESUs is that it only covers security bug fixes, and if something else turns awry in terms of the internal systems, businesses receive no external support. Continuing to rely on ESUs also means that businesses are forced to continue with their legacy systems in place, meaning that they’re limited in only being able to run with the economics and efficiency of the underlying outdated technology.

Exploring the solutions

With the deadline approaching and many businesses unaware of the alternatives available, employing the right external technology and expertise is the best method to preparing effectively. Moving applications to an updated Windows Server is no easy task however for many businesses, with complications due to old runtimes such as Java 1.3 or .Net 2.0 putting a stop to a successful switch.

Tools from an external provider, such as compatibility packages, can isolate outdated runtimes so that applications can be successfully moved to the latest supported and secure Windows Server, such as 2016 or 2019. The resulting technology container gathers the runtimes, application files, components, and deployment tools needed to ensure that older apps can run efficiently and without issue on the new server, and are easily deployed via hybrid or pure cloud platforms.

This method ensures that businesses benefit financially from both avoiding unnecessary rewrites of applications and the hefty cost of being forced to continue with ESUs. Efficiency is also gained through easier maintenance of an updated server and allowing users to complete tasks quicker and without complexity, while organisations are also able to prioritise sustainability by avoiding the need to physically replace entire systems.

Preparing for end-of-life

While preparing for the end of ESUs for Windows Server 2008 is of immediate urgency to businesses, it’s also important to take note of the emerging end-of-life roadmap that will apply to other systems over the next few years. Extended support for Windows Server 2012 will end in October 2023, and Microsoft also recently announced the end-of-support for its flagship Windows 10 operating system on 14th October 2025. What’s certainly evident is that the end-of-life treadmill will continue to turn across a range of systems as we enter the coming years, and long-term preparation at all stages will be crucial for businesses.

With the right solutions in place, achievable goals can be met within a short timeframe, meaning that for organisations it’s not too late to act immediately to ensure preparation and avoid the next expensive ESU in January 2022. Urgency is however the name of the game, and those that proactively take steps now will be able to successfully ride the large wave of end-of-life dates on the horizon.

About the Author

Mat Clothier is CEO and Founder at Cloudhouse, he leads the company ensuring that enterprises can give all their applications a future without having to needlessly re-engineer when moving existing Windows based applications to the Cloud or Windows 10. Previously Mat was Chief Technology Officer for Cloudhouse with a demonstrated history of working in the information technology and services industry. Skilled in App Virtualization, Microsoft Technologies, Managed Services, Enterprise Software, and PaaS. Mat is a strong entrepreneurship professional with a Bachelor of Science (BSc) focused in Computer Systems Networking and Telecommunications from University of Plymouth.

Featured image: ©Filins