On January 12, 2027, Microsoft ends extended support for Windows Server 2016. After that date, it stops releasing security updates, bug fixes, and technical support for the product. Mainstream support already ended in January 2022.
Servers still running 2016 will keep working, but any new vulnerability discovered after the cutoff will stay open. Many of these servers quietly run file shares, line of business applications, domain controllers, and databases, and some have been in place so long that no one remembers they are there.
Organizations have three main paths:
- Upgrade to Windows Server 2025. Upgrading in place or rebuilding is Microsoft’s recommended option and the only one that fully solves the problem.
- Move the workload to Azure. This can be simpler for older applications and removes a hardware refresh.
- Bridge with Extended Security Updates. These provide up to three years of critical and important security patches. They are a paid, temporary bridge, billed per core through Azure Arc starting January 13, 2027, and each year must be bought in order.
Most environments end up using a mix.
The place to start is the same for everyone. Find every Windows Server 2016 machine, including the forgotten ones. Check what runs on each one before choosing a target. Then pick a path for each server and set a finish date.
As an independent, vendor neutral advisory firm, CommteX Technology Advisors, LLC sits on your side of the table. We offer a cost free review to inventory your Windows Server 2016 systems and map the right path for each, then handle the hardware procurement, implementation, and Day 2 support.
Contact CommteX Technology Advisors, LLC for your free Windows Server 2016 readiness review.