Windows Server 2016 end of support: what to do?

Windows Server 2016 end of support falls on January 12, 2027, when Microsoft ends extended support. After that date, the system will keep running, but no more security updates will be released. Any flaw discovered afterward will stay open on a server that often holds the company's directory, files and business application.

This transition therefore needs to be handled as a project, not as a simple update. The server was often installed eight or ten years ago, and its hardware is reaching the end of its life too.

Windows Server 2016 end of support: the timeline

Mainstream support, which also brought improvements, ended in January 2022. Since then, only extended support has provided security updates.

Taking inventory of the server's roles

An SME server often combines several functions. Each one must be identified before choosing an option.

If an Exchange 2016 server is still running, it has not been supported since October 2025 and should be dealt with first.

• The Active Directory directory, DNS and DHCP: accounts, passwords, group policies.
• File shares and their access permissions.
• The print server and the copiers' scan folders.
• Business applications and their databases, with the version the vendor supports.
• Remote Desktop Services (RDS), if used for remote work.
• Virtual machines, if the server runs Hyper-V: each has its own operating system to check.

What are the options after Windows Server 2016?

The options can be combined: the same server can see its directory move to Entra ID, its files to SharePoint and its business application to a hosted server.

The choice depends mostly on the business applications: some require a local Windows server, others come in an online version. Ask the vendor what it supports before deciding.

• Move to Windows Server 2022 or 2025. A clean installation with role migration is often tidier than an in-place upgrade.
• Replace the server with a new machine, if the hardware is also at the end of its life.
• Host the server in a Swiss cloud: no more hardware to replace at the office, and the business application stays on Windows Server.
• Move some roles to Microsoft 365: Entra ID and Intune for accounts and computers, SharePoint and OneDrive for files, direct or cloud printing for printers.

Licenses and extended security updates

Plan for licenses: Windows Server is licensed per processor core, and client access licenses (CALs) must match the server version or a later one.

For earlier versions, Microsoft offered paid extended security updates for a limited time. If a similar offer exists for Windows Server 2016, it can cover a few months of delay on a specific server, not replace the migration.

A realistic timeline

The closer the date, the less room there is for testing. If the project has not started, the inventory is the first step to launch.

• The inventory and the choice of target, with input from the business application vendors.
• Ordering hardware or licenses, whose lead times vary.
• A full, tested backup before any work begins.
• Migration role by role, outside working hours where needed and on an agreed schedule, with a rollback plan.
• Informing users: switchover date, visible changes (network drives, printers), who to contact if something goes wrong.
• Decommissioning the old server once everything has been checked, and securely erasing its disks.