Microsoft Extends Security Updates for Windows 10 and Server 2016, but at a Price

Microsoft is giving Windows customers the "gift of time" but expects compensation for its generosity. In a community post, Microsoft confirmed it is making up to three years of Extended Security Updates (ESU) available for aging Windows installations, while remaining coy about pricing for Windows Server 2016.

Most major versions of Windows 10 reached the end of support in 2025. On October 13, 2026, it is the turn of Windows 10 Enterprise 2016 LTSB and Windows IoT Enterprise LTSB 2016. Windows Server 2016 comes to the end of the road on January 12, 2027.

Microsoft's preferred path for Windows Server 2016 customers is an upgrade to Windows Server 2025. For Windows 10 holdouts, the options are Windows 11 with its controversial hardware requirements or the final LTSC release, Windows 10 Enterprise LTSC 2021.

ESU for Windows 10 2016 LTSB is priced at $61 per device for the first year, a figure that will inexorably rise. A discount to $45 is available for customers managing devices through Intune or Windows Autopatch.

The absence of official pricing for Windows Server 2016 is frustrating for administrators unwilling or unable to move their workloads. Budgets don't plan themselves. It is unlikely to come cheap. For Windows Server 2012, Microsoft said the first year was charged at 100 percent of the full license price. The second and third years were the same and will end on October 13, 2026.

Microsoft made plenty of noise about the end of Windows 10 support last year. The Windows Server 2016 deadline has crept up more quietly, yet administrators who need breathing room to plan a migration will welcome the extra years, even at a price. A "gift of time." Just not a free one.

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Extended Security Updates Pricing Structure

Microsoft's ESU program follows a predictable pattern of escalating costs. For Windows 10 2016 LTSB, the pricing starts at $61 per device for year one, with the expectation that subsequent years will see significant increases. The company offers a $16 discount per device ($45 total) for organizations using Intune or Windows Autopatch for device management.

For Windows Server 2012, which serves as a precedent, Microsoft charged 100% of the full license price for the first year of ESU, with the second and third years maintaining the same rate. This suggests Windows Server 2016 customers could face similar or higher costs, given the newer version's likely higher base license value.

SQL Server 2016, which reaches end-of-support on July 14, 2026, starts at 75% of the full annual license price for ESU, with costs rising for each subsequent year. The final ESU cost will depend on an organization's specific licensing agreement, but customers seeking to keep security updates flowing will undoubtedly pay handsomely for the privilege.

Migration Alternatives and Challenges

Microsoft's preferred migration path for Windows Server 2016 customers is an upgrade to Windows Server 2025. However, this represents a significant undertaking for many organizations, particularly those with complex legacy applications or custom configurations.

For Windows 10 holdouts, the migration landscape is equally challenging. Windows 11's controversial hardware requirements have left many organizations unable to upgrade their existing devices. The minimum requirements include TPM 2.0, Secure Boot capability, and specific CPU generation thresholds that exclude millions of otherwise functional computers.

The alternative of moving to Windows 10 Enterprise LTSC 2021 provides a more accessible path but comes with its own limitations. LTSC (Long-Term Servicing Channel) releases are designed for specialized devices and receive only critical security updates, not feature updates. This makes them less suitable for general-purpose computing environments.

The Business Impact

For IT administrators and business leaders, Microsoft's ESU announcement presents both relief and concern. The breathing room provided by extended security updates allows organizations additional time to plan and execute migrations without compromising security. However, the escalating costs create a financial burden that many organizations must now factor into their IT budgets.

The lack of transparent pricing for Windows Server 2016 ESU is particularly problematic for budget planning. Unlike the Windows 10 pricing, which provides a clear starting point, Server 2016 customers must wait for Microsoft to reveal costs that could significantly impact their financial planning for the coming years.

Industry Context

Microsoft's approach to end-of-life transitions has evolved over the years. The ESU program, introduced to provide security updates beyond official support dates, has become a significant revenue stream for the company. While it addresses legitimate customer needs for extended support periods, it also creates a captive market where Microsoft can charge premium prices for essential security updates.

The timing of these transitions is particularly noteworthy. As organizations continue to grapple with economic uncertainty and budget constraints, the additional costs of ESU programs add another layer of complexity to IT planning. The "gift of time" comes with strings attached, and those strings are increasingly expensive.

Looking Ahead

As the Windows Server 2016 and Windows 10 2016 LTSB end-of-support dates approach, organizations must make critical decisions about their migration strategies. The availability of ESU provides a safety net, but it's one that comes at a premium price.

For many organizations, the choice will come down to balancing immediate costs against long-term strategic goals. While ESU provides a short-term solution, the escalating costs make it an unsustainable long-term strategy. The real "gift of time" may be the opportunity to plan and execute migrations properly, rather than rushing to meet arbitrary deadlines.

Microsoft's approach, while commercially understandable, highlights the ongoing tension between vendor business models and customer needs for stability and predictability in their IT environments. As the technology landscape continues to evolve, this tension is likely to remain a central theme in enterprise IT decision-making.

What This Means for Your Organization

If your organization is running Windows Server 2016 or Windows 10 Enterprise 2016 LTSB, now is the time to develop a comprehensive migration strategy. While ESU provides a temporary safety net, the costs will escalate over time, and the security risks of running unsupported software remain significant.

Consider your options carefully:

• Upgrade to current versions: While this requires investment in hardware and migration efforts, it provides the most secure and supported path forward.
• Utilize ESU strategically: If immediate upgrades aren't feasible, ESU can provide breathing room, but budget for escalating costs.
• Explore alternative solutions: Depending on your use case, cloud-based solutions or alternative operating systems might offer viable paths forward.

Whatever path you choose, the key is to act now rather than waiting until the last minute. The "gift of time" is valuable, but it's not infinite, and the costs will only increase as support deadlines approach.

The Register continues to monitor Microsoft's end-of-life announcements and their impact on enterprise IT. Stay tuned for updates on pricing, migration strategies, and industry responses to these critical transitions.