Windows licenses

Winsage
July 26, 2026
Microsoft has mandated the inclusion of the Trusted Platform Module (TPM) as a standard feature in all new motherboards and CPUs to enhance the Windows activation process. The company has introduced an enhancement to its Key Management Service (KMS) that leverages TPM's security capabilities to authenticate the legitimacy of KMS servers. This new "TPM-based attestation" aims to mitigate exploitation risks associated with KMS by validating the cryptographic integrity of KMS servers. Starting in August 2026, TPM-based attestation will be required for KMS activation with the next release of Windows Server. Microsoft has also closed off the "KMS38" activation method in 2025, while traditional KMS activation remains functional. The Massgrave collective has developed an Online KMS method that may be impacted by the new TPM-based attestation.
Winsage
June 26, 2026
Microsoft has extended the security updates for Windows 10 users by an additional year, with the new end date for the Extended Security Updates (ESU) program set for October 12, 2027. This extension applies automatically to existing ESU enrollees, and new users can sign up until the deadline. The change was confirmed by a Microsoft spokesperson in an editor's note added to a blog post. The extension does not apply to corporate Windows deployments, which require costly ESU subscriptions that extend support until October 2028.
Winsage
May 1, 2026
Leo, Richard, and Paul discussed developments in the Windows Insider Program, Snapdragon X2 gaming, artificial intelligence, and Xbox. Two changes in the Insider Program were noted. Microsoft has open-sourced early MS-DOS source code. Intel reported a .7 billion loss, which Paul attributes to 'collusion.' Microsoft and OpenAI are revising their partnership, with Microsoft 365 Copilot gaining enhanced AI features in Word, Excel, and PowerPoint, and GitHub Copilot moving to a usage-based billing model starting June 1. OpenAI is reportedly entering the mobile phone market, while Adobe's Firefly AI Assistant is in preview, and Anthropic is increasing its creator space involvement. Microsoft Gaming has rebranded to Xbox, with new leadership focused on future plans, including a mobile game store pending changes in Apple's policies. Valve will release its Steam Controller next week. A listener inquired about purchasing Windows 11 on Arm for Mac virtualization, leading to suggestions for cost-saving options. PowerToys 0.99 introduces new utilities and improvements. This week’s episode of RunAs Radio compares M365 Copilot and Claude Cowork. Reifel Rye is recommended as the brown liquor of the week.
Winsage
April 26, 2026
Months after acquiring a laptop, users may encounter a prompt from Windows 11 stating, “You’re almost done setting up your PC.” This leads to a series of inquiries about adopting Microsoft’s recommended browser settings, linking a phone for SMS notifications, and acknowledging Office installation. Users may feel compelled to click through these prompts, which can include advertisements, such as for Xbox Game Pass Premium at .99 per month. This series of prompts is referred to as the Second Chance Out of Box Experience (SCOOBE), which can resurface due to Windows updates and may lead to unnecessary support calls and potential unauthorized subscriptions in organizational settings. Users can disable SCOOBE by adjusting settings in Windows or Group Policy, but ongoing vigilance is required due to the evolving nature of Microsoft’s software.
Winsage
September 10, 2025
Microsoft and software reseller ValueLicensing are in a legal battle at the UK Competition Appeal Tribunal, which could significantly impact the second-hand software market in Europe. ValueLicensing is claiming £270 million from Microsoft, alleging anti-competitive practices that limit the availability of licenses for resale. The dispute centers on copyright laws, with Microsoft arguing that certain components of its operating system cannot be resold. The trial's outcome may set a precedent affecting the future of software resale and consumer access to affordable Microsoft products.
Winsage
September 9, 2025
A UK-based reseller's case against Microsoft regarding the resale of second-hand Windows and Office licenses is being heard by the UK’s Competition Appeal Tribunal (CAT) over three days, concluding on September 11. The court will determine if certain components of Microsoft's software are exempt from the EU’s software resale regulations, which currently allow the resale of perpetual software licenses. Microsoft argues that the resale doctrine applies only to computer programs and not to components like the graphical user interface (GUI), which they claim remain under copyright protection after license transfer. A ruling in favor of Microsoft could end the resale of second-hand Windows licenses in the UK. This case is part of a larger legal battle initiated by ValueLicensing in 2021, which accuses Microsoft of harming the pre-owned software market. The comprehensive trial is expected in 2026, but current proceedings may influence the case's direction. Additionally, with Windows 10 support ending soon, any increase in licensing costs could negatively impact users needing to upgrade their systems.
Winsage
August 2, 2025
Microsoft will discontinue updates for Windows 11 SE, a version of the operating system aimed at competing with ChromeOS in education. This was announced through a support document, which stated that Windows 11 SE will not receive the upcoming Windows 11 25H2 update. Support for Windows 11 SE, including updates and security fixes, will end in October 2026. Microsoft recommends users transition to devices that support other editions of Windows 11 for ongoing support.
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