Planning for the Windows Server 2016 end of support

Microsoft has announced the Windows Server 2016 end of support on January 11, 2027. If your organization is still running on this platform, it’s important to plan your next steps as soon as possible.

What End of Support Means for Your Business

Continuing to run Windows Server 2016 past January 11, 2027, without a proper plan introduces significant risks for your organization:

Security vulnerabilities: Without security updates, any newly discovered security gap or vulnerability will remain unattended by Microsoft, creating a major entry point for cyberattacks.

Compliance issues: Many regulatory standards (like HIPAA, GDPR, PCI-DSS) require the use of supported software. Running an outdated Operating System can lead to compliance failure.

Performance Degradation: Updates and optimizations keep servers running smoothly. Without support by Microsoft, server performance deteriorates, affecting your organization’s productivity.

Your Options

Planning your next steps in a timely manner will keep your organization secure, without much disruption to your operations. Depending on your specific needs, there are several courses of action you might take.

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Plan, deploy and/or optimize your cloud, hybrid, or on-premises environment

Upgrade to the newest Windows server

Windows Server 2025 includes advanced features improving security, performance and flexibility. Upgrading from Windows Server 2016 to 2025 will improve your organization’s workflow and ensure you receive the latest updates for streamlined infrastructure management. You can upgrade directly from Windows Server 2016 to 2025.

Migrate to the Cloud

Moving your ecosystem to Azure Virtual Machines is another viable option to ensure your organization stays up-to-date. If your servers are running on Windows Server 2016, you can continue running them as you migrate to Azure. With the added cloud innovation come several benefits over on-premises servers:

Constant security updates.

Critical security updates on Windows Server after end of support (for a certain period).

Upgrades included with Azure.

Ability to adopt more cloud services over time.

If this is the best option for your organization, feel free to contact us for guidance on your Azure migration.

Next Steps

Taking a proactive approach and planning before the Windows Server 2016 end of support will ensure a successful migration with limited impact on operations. Generally, these are some key steps to take into consideration: