Windows Server 2016 reaches end of support on January 12, 2027. Windows Server 2012 R2 lost support in October 2023, and its final year of paid Extended Security Updates ended October 13, 2026. ITsoft moves your servers, file shares, applications and Active Directory to Windows Server 2025 or Azure, with a tested plan and as little disruption as possible.
Get a Free Server Upgrade Assessment
Where does your server stand?
| Version | Status |
|---|---|
| Windows Server 2012 / 2012 R2 | Out of support since Oct 10, 2023. Paid security updates ended Oct 13, 2026 |
| Windows Server 2016 | Support ends January 12, 2027 |
| Windows Server 2019 / 2022 | Supported |
| Windows Server 2025 | Supported, newest |
After end of support, Microsoft stops releasing security fixes. Unpatched servers are a common entry point for ransomware, and cyber insurers and auditors increasingly ask about them. Microsoft offers paid Extended Security Updates for Windows Server 2016 through Azure Arc, but it’s a temporary bridge that costs money every year you delay.
Your options
- Upgrade to Windows Server 2025 on new hardware or a VM: the most common path. We migrate roles, data and applications to a fresh, supported server.
- Move to Azure: run your servers as Azure virtual machines, and stop buying and maintaining hardware.
- Retire the server: some old servers only run file shares or a single app that can move to Microsoft 365, SharePoint or a cloud service.
- Hybrid: keep critical workloads on-site and move the rest to Azure.
What our Windows Server migration service includes
- Server inventory: roles, shares, permissions, applications, scheduled tasks, printers and dependencies
- Active Directory and DNS migration: domain controllers moved and verified without breaking logins
- File server migration: data and permissions copied intact, with mapped drives updated
- Application testing: we confirm line-of-business apps (accounting, ERP, custom software) run on the new server before cutover
- SQL Server databases: upgraded at the same time if needed
- Backups and security hardening: new backups tested, and the server configured to current security baselines
- Decommissioning: the old server is safely wiped and retired
How a Windows Server upgrade works
- Free assessment: we inventory your servers and identify what’s at risk.
- Plan: you get a written scope, timeline and cost estimate, including hardware or Azure costs.
- Build and test: we build the new server and test applications with your team.
- Cutover: we migrate during a planned after-hours window and verify everything works Monday morning.
- Support: we monitor the new server and handle any follow-up issues.
Why ITsoft
- Over 20 years of Windows Server and SQL Server work, so servers and databases are upgraded together, by one team
- Tested before cutover: nothing goes live until your apps work on the new server
- Remote and nationwide, with onsite help available in the Oklahoma City area
- A written estimate before any work starts, so you know the cost up front
Related reading: Windows Server 2016 end of support · Windows Server 2012 R2 end of life · Managed IT services
Windows Server upgrade FAQs
What happens if we keep running Windows Server 2016 after January 12, 2027?
It keeps working, but Microsoft stops releasing security updates unless you pay for Extended Security Updates. Each month without patches increases the risk of a breach, and some software vendors and insurers stop supporting unpatched systems.
Can we upgrade in place from 2016 to 2025?
Sometimes, but we usually recommend a clean migration to a new server or VM. It avoids carrying old problems forward and gives you an easy rollback if something goes wrong.
How long does a server migration take?
A single file or application server is often planned and migrated within a few weeks. Environments with several servers, domain controllers and custom applications take longer. You’ll get a timeline after the assessment.
Is moving to Azure cheaper than buying a new server?
It depends on how many servers you run and how long you keep hardware. We compare both on a 3–5 year basis in the assessment.
Get a free Windows Server upgrade assessment
Tell us which servers you’re running, and we’ll give you a clear plan to get supported before January 12, 2027.
