Microsoft gives Windows laggards the 'gift of time' wrapped in licensing fees

With Server 2016 and other OSes for the chop, security fixes can continue to flow for 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.

SQL Server 2016, for which support ends on July 14, 2026, starts at 75 percent of the full annual license price, 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.

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. ®