Microsoft Warns Enterprises as Legacy Windows Versions Near End of Support
With support deadlines approaching for several legacy Windows editions, organizations must decide between timely upgrades and rising ESU costs.
Key Takeaways:
- Multiple legacy Windows versions are nearing end of support, increasing security risk exposure.
- Microsoft is offering paid ESUs, but costs rise annually and are cumulative.
- Organizations must balance upgrade timelines against escalating ESU expenses.
Microsoft’s newly announced end-of-support deadlines for several legacy Windows platforms have triggered heightened urgency across enterprise IT environments. As security patches and technical support near expiration, organizations are under increasing pressure to remediate risk exposure before unpatched vulnerabilities create operational and compliance liabilities.
The Windows 10 Extended Security Updates (ESU) program gives organizations a simple fallback option when they aren’t able to upgrade older systems before support ends. This paid offering allows businesses to continue receiving critical and important security updates for Windows 10 beyond its end‑of‑support date. It helps organizations maintain essential protection while they plan a move to a newer LTSC release or Windows 11.
Upgrade guidance for Windows 10 LTSB and IoT Enterprise
In a recent blog post, Microsoft mentioned that three more versions of Windows will reach end of support within the next few months. Going forward, these older versions will no longer receive security patches, non‑security updates, bug fixes, or technical support. However, organizations will have the option to buy ESUs to continue receiving security updates.
Microsoft recommends Windows 10 Enterprise 2016 LTSB customers upgrade to a more recent LTSC release for Windows 10 or Windows 11 by October 13, 2026. After this date, organizations that remain on the older version will be able to instead opt to buy up to three years of Extended Security Updates. These ESUs begin at $61 per device annually, with a reduced rate of $45 per device for devices managed through Intune or Autopatch, and the cost increases each year. Microsoft notes that ESUs are cumulative, and enrolling in a later year requires paying for previous years as well.
Additionally, Windows 10 IoT Enterprise 2016 LTSB customers are advised to move to the newest IoT LTSC version available for Windows 10 or Windows 11. For organizations that cannot upgrade immediately, Microsoft recommends contacting their IoT device manufacturers or OEM partners to obtain details on pricing and availability for ESUs and to enroll if needed.
Microsoft recommends Windows Server 2016 customers upgrade to Windows Server 2025 before support ends on January 12, 2027. If upgrading isn’t immediately possible, ESU coverage can be purchased for up to three additional years. However, Microsoft has yet to share the pricing and availability details.
Budgeting and operational impact of delayed modernization
As organizations prepare for the upcoming end‑of‑support deadlines, it becomes clear that delaying upgrades carries more than just security risks. However, it also introduces significant budgeting and operational pressures tied to the escalating cost of Extended Security Updates. IT teams supporting large fleets must navigate not only rising annual expenditures but also the cumulative payment requirement for late enrollment, which adds another layer of financial complexity.
Organizations can better evaluate whether short‑term ESU coverage or timely modernization offers the most sustainable path forward by acknowledging how these compounding costs influence planning and resource allocation.
Rabia has a master's degree in Software Engineering and she has years of experience writing professionally about Microsoft products and other technologies. Rabia has also written for OnMSFT.com as well as Windows Report. She is always up to date on t...
