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

The Register

February 24, 2026

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Microsoft has introduced Extended Security Updates (ESU) for aging Windows systems, offering up to three years of extended support for older versions like Windows Server 2016 and Windows 10 LTSB. This "gift of time" comes at a cost, with pricing starting at $61 per device for the first year of ESU for Windows 10 2016 LTSB, increasing in subsequent years. While discounts are available for managed devices using Intune or Autopatch, the lack of official pricing for Windows Server 2016 leaves administrators uncertain about their budgeting. This move by Microsoft provides much-needed flexibility for organizations struggling to migrate older systems but signals that staying on outdated software will require significant financial planning. The end-of-support dates for major Windows versions are looming, with Windows Server 2016 set to reach its limit in January 2027 and Windows 10 Enterprise 2016 LTSB following suit in October 2026. Microsoft is encouraging upgrades to newer versions like Windows Server 2025 or Windows 11, though the latter’s hardware requirements have raised concerns. For those choosing to stay on older systems, ESU offers a paid pathway for continued security updates, with pricing structured to rise annually. This model reflects Microsoft’s shift toward monetizing extended support rather than offering it freely, as was previously done in some cases. For businesses reliant on legacy systems, the decision to upgrade or purchase ESU is critical. While ESU provides valuable time to plan migrations, the rising costs make it a costly extension. Organizations must weigh the short-term savings of delayed migration against the long-term expense of extended support. For those unable to migrate immediately, ESU offers a lifeline but with financial implications that demand careful budgeting and strategic planning. The significance of this announcement lies

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Originally published on The Register on 2/24/2026