Windows Server 2016 reaches end of support on 12 January 2027. That’s less than three months away.
After that date, Microsoft stops releasing security updates, bug fixes, and technical support for it. Servers will keep running, but every new vulnerability found from then on stays open.
If your business still runs file servers, line-of-business applications, or domain controllers on Server 2016, now is the time to plan the move.
What Does End of Support Mean?
Windows Server follows Microsoft’s Long-Term Servicing Channel: five years of mainstream support, then five years of extended support. For Windows Server 2016, that ten-year window closes on 12 January 2027.
From that date, Server 2016 will no longer receive:
- Security updates
- Bug fixes
- Technical support from Microsoft
The only way to keep receiving security patches after that is through paid Extended Security Updates (ESUs), which we cover below.
The Risks of Staying on Server 2016
An unsupported server is an easy target. Attackers watch for end-of-support dates because they know unpatched systems will stay vulnerable.
Security exposure. Any vulnerability discovered after 12 January 2027 will never be fixed. Servers hold your most sensitive data, so one weak server can put the whole network at risk.
Compliance problems. Cyber Essentials requires software to be supported and patched. Running Server 2016 past its end date without ESUs puts your certification at risk, and with it any contracts that depend on it.
Cyber insurance. Insurers increasingly ask about unsupported systems. Outdated servers can affect your cover or a future claim.
Application compatibility. Software vendors stop supporting their products on old operating systems, leaving you stuck on old versions too.
Ageing hardware. Many Windows Server 2016 machines are now eight or more years old. The risk of hardware failure rises every year.
Your Three Options
1. Upgrade to Windows Server 2025
This is Microsoft’s recommended route. From Windows Server 2025, non-clustered servers can upgrade in place directly from Server 2016, keeping roles, applications, and data.
You’ll need a valid Windows Server 2025 licence, and your hardware must meet the new requirements. For domain controllers, the safer approach is to build a new 2025 server and migrate roles across rather than upgrading in place.
If your hardware is near the end of its life, a fresh build on new kit is often the better long-term choice.
2. Move to the Cloud
Migrating workloads to Microsoft Azure removes the need to manage physical servers. Windows Server 2016 virtual machines running in Azure receive ESUs free of charge, giving you time to modernise once you’ve moved.
It’s also a good moment to ask whether some workloads need a server at all. File shares, for example, can often move to SharePoint or OneDrive. Our cloud solutions team can help you decide.
3. Buy Extended Security Updates
If you can’t move in time, ESUs keep Critical and Important security patches coming for up to three years, until January 2030. For on-premises servers, they’re delivered through Azure Arc on a pay-as-you-go basis.
ESUs are a stopgap, not a strategy. They don’t include new features, non-security fixes or technical support, and the cost adds up over time.
| Option | Best for | Things to consider |
|---|---|---|
| Upgrade to Server 2025 | Businesses keeping servers on site | New licences; hardware may need replacing |
| Move to Azure | Businesses ready to reduce on-site kit | Ongoing cloud costs; free ESUs while you modernise |
| Extended Security Updates | Critical apps that can’t move yet | Security patches only; temporary fix |
Your Migration Plan: Step by Step
- Audit your servers. List every server running Windows Server 2016, including virtual machines. Note what each one does and who relies on it.
- Check your applications. Confirm with each software vendor that their product supports Windows Server 2025 or your chosen cloud platform.
- Review your hardware. Check whether existing servers meet Server 2025 requirements and how long they have left.
- Choose a route for each server. Upgrade, move to the cloud, retire it, or cover it with ESUs while you plan.
- Back everything up. Take a full, tested backup before you change anything.
- Test first. Run the upgrade or migration on a test server or low-risk system before touching critical ones.
- Schedule the work. Plan upgrades out of hours to keep disruption to a minimum.
- Decommission safely. Securely wipe and recycle old hardware so no data is left behind.
Start now. Licences, hardware lead times and vendor checks can all take longer than expected, and January is close.
How Sprint Integration Can Help
We provide managed IT support in London, Essex and the South East, helping businesses move off ageing systems with minimal disruption. We can help with:
- Server audits and readiness assessments
- Windows Server 2025 upgrades and migrations
- Moving workloads to Azure, SharePoint and OneDrive
- Extended Security Updates setup through Azure Arc
- Backup before, during and after migration
- Secure disposal and recycling of old hardware
Not sure where your servers stand? Book a free IT Health Check and we’ll review your setup.
Windows Server 2016 has served businesses well for a decade, but 12 January 2027 is a fixed deadline. Plan now and you choose the route, the timing and the budget. Leave it late and you’re left paying for ESUs or running unprotected servers.
FAQs
When does Windows Server 2016 support end?
Extended support ends on 12 January 2027. After that, Microsoft stops releasing free security updates.
Will my server stop working after 12 January 2027?
No, it will keep running. But it won’t get security updates, fixes or support, leaving it exposed to new threats.
Can I upgrade directly from Windows Server 2016 to Windows Server 2025?
Yes, for non-clustered servers. You’ll need a Server 2025 licence and compatible hardware.
How long do Extended Security Updates last?
Up to three years, until January 2030. They cover security patches only, so they’re a short-term fix.
Are Extended Security Updates free in Azure?
Yes, for eligible servers running in Azure. On-premises servers need paid ESUs through Azure Arc.
