If your organization is still running Windows Server 2016, you’re not alone. Many businesses continue to rely on it for file services, Active Directory, and critical business applications. In most environments, these servers are still stable and doing their job. So why should you replace them? The primary concern isn’t performance. It’s what changes once Windows Server 2016 reaches end of support. Those changes introduce risks that are often underestimated.
What does “End of Support” mean for Windows Server 2016?
When Windows Server 2016 reaches end of support, Microsoft will no longer provide:
- Security updates or patches
- Vulnerability fixes
- Mainstream technical support
When a system goes “end of support” or “end of life,” it’s not liks a switch is flipped. Your server doesn’t suddenly stop working, but it does immediately become unsupported infrastructure, which carries a very different risk profile. From that point forward, any newly discovered vulnerability remains unpatched, and recovery options become more limited.
Keeping IT systems current is one of the easiest things you can do to reduce your organization’s risk and exposure to cybersecurity threats.
Technically, mainstream support for Windows Server 2016 ended in 2022, but even if you purchased ESUs (extended security updates), that coverage is coming to an end in January of 2027. That’s why taking action in 2026 is so important.
“It Still Works” Doesn’t Mean It’s Still Safe
Just because it works, doesn’t mean it’s secure. An older system still working fine is a sign of good IT management, but historical stability doesn’t reduce future risk once a platform is unsupported. The operating system doesn’t need to fail for your risk to increase.
Unsupported systems:
- Accumulate unpatched vulnerabilities
- Become easier targets for threat actors over time
- Require more complex defense measures
The longer a server remains unsupported, the harder it becomes to justify from a security standpoint. Even if it’s functional, it’s not secure.
The Biggest Risk of an Unsupported Server Is Recovery
Day-to-day operations often look unchanged after end of support. The real consequences often only show up during an incident.
When a supported Windows Server fails, your IT provider or team has reliable options, like vendor-recommended fixes, current documentation, and supported recovery paths. Those options aren’t available with an unsupported system.
When an unsupported Windows Server fails, vendor assistance may be limited or unavailable, fixes can involve high risk workarounds, and your recovery timelines become less predictable. Things like your recovery time objective (RTO) and your recovery point objective (RPO) are impacted, putting your backup and disaster recovery strategy at risk unnecessarily.
Unsupported systems don’t fail more often, but they do fail harder when something goes wrong.
Security and Compliance risks grow over time
Running an unsupported version of Windows Server introduces long-term security concerns. Newly discovered vulnerabilities may never be patched. Attackers have more time to analyze weaknesses, since the system isn’t being updated. It becomes a fixed target, unable to evolve at the same speed cybersecurity threats and threat actor techniques do. Once that happens, you’re relying on your security tools to compensate for missing OS protections.
Over time, this leads to problematic audit findings, cyber insurance complications, questions from leadership, and more exposure during a cybersecurity incident investigation.
Even strong security controls can’t offset the risks of an unpatched infrastructure.
Delaying Windows Server 2016 Planning Reduces Your Options
Many organizations assume that waiting preserves flexibility. Delaying actually leads to:
- Fewer upgrade paths
- Tighter timelines
- Higher costs
- Reactive decision-making
Alternately, early planning helps organizations:
- Prioritize business critical systems
- Use a road map or project plan to work in phases
- Strategically align projects with budgets and organizational goals
- Reduce disruption to your day-to-day operations
Waiting doesn’t eliminate the work, it removes control over how and when it happens. Our recommendation is always to take a proactive, strategic approach. When you’re evaluating your aging server in terms of your entire environment, you’re able to make decisions that help you align to your long-term goals rather than rushing to implement a quick fix without looking through the lens of your desired future state.
Unsupported servers create business risk, not just IT risk
Once Windows Server 2016 is out of support, infrastructure risk becomes a business conversation, not just a technical one.
Questions shift from things like: “Is the server stable?” to:
- “What happens if this fails?”
- “Are we exposed to cybersecurity threats?”
- “Why wasn’t this addressed earlier?”
At that point, decisions are often made under pressure. That’s exactly when risk is hardest to manage, and why we try to take a more proactive approach.
Planning starts with visibility, not an upgrade
Addressing Windows Server 2016 end of support doesn’t mean upgrading everything immediately. The first step is a discovery period focused on understanding your unique environment and how embedded Windows Server 2016 is.
Work with your internal IT team or MSP to identify:
- Which servers are still running 2016?
- What systems and users depend on them?
- Which servers present the highest risk?
- Which servers can be addressed over time?
That visibility helps you reduce uncertainty and make informed decisions about your next steps.
Windows Server 2016 Readiness Assessment
Our Windows Server 2016 Readiness Assessment helps organizations:
- Identify unsupported or at-risk servers
- Evaluate security and recovery implications
- Build a practical, strategic plan for what’s next
This isn’t about creating urgency for urgency’s sake. It’s about providing clarity, reducing risk, and ensuring you have a proactive plan in place.
The assessment begins with a guided conversation with our Engagement Team. For fully managed clients, we leverage our in-depth knowledge of your environment to evaluate how Windows Server 2016 impacts your infrastructure, security posture, and long-term IT strategy. For other organizations, we perform a structured review to assess current risks and opportunities.
You’ll receive a clear, actionable roadmap outlining your options, recommended next steps, and how we can support you through the transition.
Still running Windows Server 2016?
If your environment includes Windows Server 2016, now is the right time to assess risk and plan next steps. It’s important to take action in 2026, before support ends.
Schedule a Windows Server 2016 Readiness Assessment
We promise clear answers, practical options, and no pressure to upgrade before you’re ready. Reach out to us to schedule your Readiness Assessment today!
Frequently Asked Questions
When does Windows Server 2016 reach end of support?
Windows Server 2016 reaches end of support on January 12, 2027. After that date, Microsoft will no longer provide security updates for Windows Server 2016 under standard support. Mainstream support ended January 11, 2022.
What happens when Windows Server 2016 is out of support?
When Windows Server 2016 is out of support, it can continue running, but it will no longer receive security patches. That means newly discovered vulnerabilities remain unpatched, increasing risk over time.
Is it safe to keep running Windows Server 2016 after end of support?
Running Windows Server 2016 after end of support increases risk. Even if the server is stable, the lack of security updates makes it harder to protect against emerging threats. It’s also harder to justify for compliance, insurance, and audit requirements.
What are the biggest risks of running an unsupported server?
The biggest risks are unpatched vulnerabilities, higher threat exposure, and more challenging recovery during incidents. Unsupported servers also create challenges with compliance, vendor support (like MSPs and third parties), and cyber insurance reviews. Many MSPs do not support operating systems that are unsupported by the vendor, which adds another layer of complexity and risk.
Why does “unsupported” matter if the server is working fine?
Because “working fine” describes today’s performance, not tomorrow’s risk. Once support ends, the platform’s security posture stops improving. Threats continue evolving, which reduces your margin for error.
How can an unsupported server impact compliance or cyber insurance?
Unsupported systems raise red flags during audits and insurance reviews because they indicate known risk. There’s inherent exposure without vendor security updates. Organizations must document compensating controls or remediation plans if unsupported systems remain in use.
What’s the first step to address Windows Server 2016 end of support?
The first step is an inventory and dependency review. Identify which servers run 2016, what roles they support, what depends on them (people and applications), and which systems carry the highest risk. Our Readiness Assessment is a great start. From there, you can build a phased plan.
How far in advance should we plan a Windows Server upgrade?
Ideally, start planning 12–18 months ahead. That timeline allows for discovery, application testing, phased rollouts, and budgeting without forcing rushed changes. Given the impending deadline, addressing this in 2026 is crucial.
Do we need to upgrade every Server 2016 system at once?
No. Most organizations take a phased approach. Prioritize high-risk or high-impact systems first, then schedule remaining upgrades based on business cycles, application readiness, and budget.
What is a Windows Server 2016 Risk & Readiness Assessment?
A Windows Server 2016 Readiness Assessment identifies where Server 2016 exists in your environment, evaluates your risk, and provides a practical roadmap so you can plan upgrades on your timeline.
