Windows Server 2016 end of support

Windows Server 2016 support ends January 12, 2027. Get your migration plan now.

After that date, Microsoft stops patching Windows Server 2016. We find every affected server, recommend the right path for each one and help you move before the deadline, without disrupting your business.

63 days until support ends
Why it matters

Your servers keep running. Your protection does not.

No more security patches

New vulnerabilities stay open, and attackers actively look for unsupported servers.

Insurance and compliance gaps

Cyber insurance forms and customer security reviews ask whether you run supported software.

Less vendor support

Application vendors stop supporting their products on old operating systems.

Rushed, risky migrations

Leaving it to December means less testing, longer downtime and higher cost.

Your options

Three ways forward, chosen server by server.

Upgrade in place

Move to a current Windows Server version on your existing hardware when it is healthy and your applications support it.

Move to Azure

Replace aging hardware with Azure virtual machines, with backup and disaster recovery built in.

Retire or replace

Move file shares to SharePoint and OneDrive, or switch a workload to a cloud service so the server can go.

Paid Extended Security Updates can buy time for a server that cannot move before the deadline, but they are a short-term bridge, not a plan. Pricing and eligibility depend on your licensing, so we confirm current terms with you.

Fixed-price assessment

Know exactly what to do, what it costs and when.

A short review of your environment with a price agreed before we start. You keep the plan whether or not you work with us on the migration.

  • An inventory of every affected server, including forgotten ones
  • An application compatibility check, including SQL Server 2016
  • The recommended path for each server, with a cost comparison
  • A week-by-week plan to finish before January 12, 2027
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The plan

There is still time, if you start now.

  1. Weeks 1–2Inventory every server, its applications and its business owner.
  2. Weeks 3–4Test compatibility and choose upgrade, Azure or retire for each workload.
  3. Weeks 5–7Migrate in small, tested steps, riskiest servers first, each with a rollback plan.
  4. Week 8Validate, document and switch off the old servers.
Questions

Windows Server 2016 end of support FAQs

Will our Windows Server 2016 servers stop working on January 12, 2027?

No. They keep running, but Microsoft stops releasing regular security updates. Every new vulnerability found after that date stays open unless you pay for Extended Security Updates.

Do we have to move everything to the cloud?

No. We decide server by server. Upgrading in place is often right when the hardware is healthy and your applications support a newer Windows Server. Azure makes sense when the hardware is also aging or you want less on-site maintenance.

What if we cannot finish before the deadline?

We move the riskiest servers first, such as anything reachable from the internet or holding sensitive data. Paid Extended Security Updates can bridge a server that needs more time. Pricing and eligibility depend on your licensing, so we confirm current terms before you rely on them.

What does the assessment cost?

It is a fixed price agreed before we start, based on how many servers you have. There are no surprises, and you keep the plan whether or not you work with us on the migration.

Can you also handle SQL Server 2016?

Yes. SQL Server 2016 already reached the end of extended support in July 2026, so database servers often need attention for two reasons. We include it in the assessment.

Get a fixed-price assessment