The Server Refresh Deadline for Windows Server 2016

28 Jan The Server Refresh Deadline for Windows Server 2016

Posted at 12:00h in Cloud, TCT News by TCT

Time moves fast in the world of technology, and operating systems that once felt cutting-edge are becoming obsolete. With Microsoft having set the deadline for Windows Server 2016 End of Support to January 12, 2027, the clock is ticking for businesses that use this operating system. Once support ends, Microsoft will no longer provide security updates or patches, leaving your business systems vulnerable. It’s not just about missing new features, continuing to use unsupported software significantly increases the risk of cyberattacks. If your systems are still on Windows Server 2016, now is the time to plan your upgrade. With about a year until support ends, waiting until the last minute can lead to rushed decisions and higher costs.

Understanding the Security Implications

When support ends, the protection provided by security updates and patches disappears, as Microsoft will no longer fix bugs or vulnerabilities. Hackers often target unsupported systems, knowing any new exploits will go unpatched and open the door to attacks. Legacy systems put IT administrators in a tough spot. Without vendor support, defending against threats becomes nearly impossible, compliance with industry regulations is compromised, and running unsupported software can lead to failed audits. Additionally, customer data on servers running this operating system is vulnerable to theft and ransomware. The cost of a breach far outweighs the cost of upgrading. Using unsupported systems is like driving a faulty, uninsured car, failure is inevitable. The question isn’t if it will happen, but when.

The Case for Cloud Migration

Businesses can either buy new servers or migrate to the cloud. New hardware is expensive and locks you into fixed capacity for years. Cloud platforms like Azure and AWS offer scalable resources, pay‑as‑you‑go pricing, better reliability, and built‑in infrastructure management. This frees your IT team to focus on strategic work instead of hardware maintenance.

Analyse Your Current Workloads

Before moving to the cloud, it’s essential to know what you’re working with. Take inventory of all applications running on your Windows Server 2016 machines. While some are cloud-ready, others may need updates or reconfiguration. Identify which workloads are critical to your daily operations and prioritise them in your migration plan. You may also discover applications you no longer need, making this an ideal time to streamline and clean up your environment. When in doubt, consult with your software vendors to confirm compatibility, as they might have specific requirements for newer operating systems. Gathering this information early helps you to avoid surprises during the actual migration.

Plan a Phased Migration

Avoid “big bang” transitions. Move low‑risk workloads first, then gradually migrate higher‑impact systems. Set a timeline well ahead of the support deadline and communicate clearly with staff to prevent confusion and downtime.

Test and Validate

After migrating each workload, confirm that applications run correctly, users can access data, and performance meets expectations. Adjust cloud resources as needed for optimal speed. The summarised steps for a successful migration include:

Audit all current hardware and software assets
Choose between an on-premise upgrade or a cloud migration
Back up all data securely before making changes
Test applications thoroughly in the new environment
Do not declare victory until users confirm everything is working

The Cost of Waiting

Ignoring the end of support deadline is not a viable strategy. Some businesses hope to delay until the last minute and then rush a migration, but this is extremely risky. Cybercriminals constantly target outdated, vulnerable systems, often using automated bots to scan for weaknesses. If you continue using Windows Server 2016 past the extended support dates, you may need to purchase ‘Extended Security Updates.’ While Microsoft offers this service, it is extremely costly, and the price rises each year, making it more a penalty for delay than a sustainable long-term solution.

Take Action Now

With Windows Server 2016 reaching end of support, upgrading is essential. Whether you choose new hardware or the cloud, acting now protects your data and modernises your infrastructure. If you need help planning or migrating, we specialise in smooth, secure upgrades—reach out today to get started.

Robert Brown
28/1/2026