As most probably already know, 12 January 2027 marks the point at which Microsoft ends extended support for Windows Server 2016.

It’s been a good innings for the operating system, but on calling time, there’s a potential advantage in switching off old servers and moving to either serverless applications, or Software as a Service replacements.

The question isn’t so much about upgrading a server, but more about the workload, and if it could be done better with modern technology. That may mean Windows Server 2025, it could be Azure, it could be SaaS. Best case scenario, it could be simply turning the server off.

Curtains on extended support means there will be no further standard security updates, patches, or technical support from Microsoft. As always, Microsoft has signalled the end for some time.

Extended Security Updates can extend the deadline

For those still running Windows Server 2016, the obvious discussion is if Windows Server 2025 is on the cards, or if purchasing (expensive) Extended Security Updates is an option.

Those are important questions, but we're increasingly seeing customers consider eliminating the servers altogether. Where feasible, this is a preferred option; most IT environments carry infrastructure that has outlived its original purpose, so any opportunity to leave that in the past where it belongs, is a good one.

In any case, servers deployed a decade ago often find themselves lightly used, or even redundant (and almost certainly obsolete). Quite often, these machines hang around past their use-by date out of convenience, or as relics of since-changed business processes – a file server because SharePoint Online wasn't yet adopted, an application server running in the background but rarely accessed...you get the idea.

Already our Customer Success team are reporting that their discussions around Server 2016 are surfacing minor Eureka moments, where a closer look at the infrastructure offers an opportunity to evaluate whether those workloads should continue to exist in their current form.

In many cases, the answer is no.

Not every server needs a replacement

Traditionally, infrastructure refreshes followed a familiar pattern. Old server becomes new server, physical server becomes virtual server, Windows Server 2016 becomes Windows Server 2025.

While that is sometimes the case, modern cloud services offer a simpler alternative.

Emerging use cases include replacing:

• File servers with SharePoint Online and OneDrive for Business
• Remote Desktop Services with Desktop as a Service (DaaS) solutions
• On-premises identity services with Microsoft Entra ID
• Legacy business applications with cloud-native platforms or SaaS alternatives
• Application servers with event driven serverless architectures and automation platforms

Less is always more with infrastructure, and fewer servers means lower operating costs, reduced management overhead, and a smaller security footprint.

Modernisation vs operating system upgrade

As it does, Microsoft has announced Extended Security Updates (ESUs) for Windows Server 2016, providing additional time for those unable to migrate off the old platform before the EOL deadline.

That flexibility can be valuable for business-critical applications where immediate change isn't practical. But they should be seen as a temporary bridge rather than a long-term strategy, because even the ESUs will eventually halt. This option is comforting for those that need to protect workloads while delivering on their modernisation journey.

As January 2027 approaches, it’s a conversation worth having. Get in touch and let’s explore the options for your Windows Server estate.