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Winsage
October 12, 2026

Microsoft Warns About Windows Update Certificate Expiration

Microsoft has reminded IT administrators about the expiration of certificates that enable trusted connections between Windows devices and Windows Update servers, set to expire in May and June of 2027. Devices without replacement certificates by these deadlines may lose access to Windows Update services. Most supported Windows devices will receive new certificates automatically through security updates, but older or infrequently updated systems may require manual intervention. Organizations that do not update their devices risk losing access to critical updates, particularly unsupported Windows versions that will not receive necessary certificate updates. IT teams should audit device inventories and ensure compliance with updates, as systems on supported versions will obtain replacement certificates seamlessly. Upgrading unsupported systems is essential, and organizations are encouraged to conduct audits and expedite upgrade projects to avoid losing access to Windows Update.
Windows 11 24H2 hits end of updates Oct. 13: What you should do now
Winsage
October 12, 2026

Windows 11 24H2 hits end of updates Oct. 13: What you should do now

Windows 11 version 24H2 for Home and Pro systems will stop receiving security updates on October 13, 2026. After this date, these editions will not receive any updates or technical support, although they will still boot. Windows 11 Enterprise, Education, IoT Enterprise, and Enterprise multi-session editions will continue to receive support until October 12, 2027. Organizations are advised to verify their systems' versions and editions, especially for those without endpoint management systems. Windows 11 25H2 and 26H2 are available as upgrade options, with 25H2 supported until October 12, 2027, and 26H2 supported until October 10, 2028, for Home and Pro editions. The rollout of 26H2 will be phased, and safeguard holds may be implemented if compatibility issues are detected. Unmanaged Home and Pro devices on 24H2 will automatically receive 25H2, while managed devices may require IT intervention. Regular monitoring and proactive management of Windows versions are necessary to ensure compliance and avoid future deadlines.
Windows 11 version 26H2 is rolling out now — here’s how to get the update now and get the most out of the 2026 update
Winsage
October 11, 2026

Windows 11 version 26H2 is rolling out now — here’s how to get the update now and get the most out of the 2026 update

Microsoft is gradually introducing the Windows 11 2026 Update (version 26H2) to compatible devices. The update is optional and requires manual installation for users who want it before the general rollout. Users on versions 25H2 or 24H2 can update without a complete reinstallation, while those on version 23H2 or earlier must perform a full in-place upgrade. To install the update from Settings, users should open Settings, click on Windows Update, enable the toggle for getting the latest updates, check for updates, download and install, and restart the device. If the upgrade option is not visible, it may indicate incompatibility. The Media Creation Tool can be used for creating bootable USB media for users upgrading from older versions like 23H2 or Windows 10, but it requires a complete reinstallation. Steps include downloading the tool, selecting the USB drive option, and following prompts to create the installation media. Users can also download the Windows 11 version 26H2 ISO file from the Microsoft support website, mount the ISO, and run setup.exe to complete the installation.
Windows 11 annual update is boring, but staying on 24H2 is a security risk
Winsage
October 10, 2026

Windows 11 annual update is boring, but staying on 24H2 is a security risk

Microsoft has released Windows 11 26H2 as a low-disruption update that activates existing features for users who have kept up with monthly updates. Users on version 24H2 should upgrade soon, as support will end on October 13, 2026, and they will no longer receive security patches. The end of support for various Windows 11 versions is as follows: 26H2 on October 9, 2028; 26H1 on March 14, 2028; 25H2 on October 12, 2027; and 24H2 on October 13, 2026. The 26H2 update includes new security features, Start menu customization, and improvements to File Explorer and AI integration. Users must have 24H2 or 25H2 installed to access the update, which may not be available to all devices due to compatibility safeguards. It is recommended to create a System Restore Point before updating.
Microsoft: Outdated Windows devices will stop receiving security updates
Winsage
October 9, 2026

Microsoft: Outdated Windows devices will stop receiving security updates

Microsoft will stop providing security updates for devices running unsupported versions of Windows after the Windows Update certificate rotation in May and June 2027, specifically on May 17, 2027, and June 19, 2027. Users and administrators are advised to upgrade to a supported version of Windows before these dates to maintain system integrity. Replacement certificates have already been issued for supported versions, requiring no action for those systems. Specific upgrade guidance includes: - Windows 11, version 25H2 and later: No action required. - Windows 11, version 24H2 and Windows Server 2025: Install the September 2025 security update or later before June 19, 2027. - Other supported versions of Windows 11, Windows Server 2022, and Windows 10: Install the July 2026 security update or later before June 19, 2027. - Windows 10 Enterprise 2019 LTSC, Windows Server 2019, and Windows Server 2016: Install the July 2026 security update or later before May 17, 2027. - Other Windows versions: Upgrade to a supported version of Windows client or Windows Server. IT administrators should evaluate their networks for unsupported Windows versions and ensure monthly updates are applied to supported devices. The directive does not apply to devices receiving updates through Windows Server Update Services (WSUS). Microsoft also announced the rollout of Windows 11, version 26H2, as an enablement package for eligible systems.
From searching to doing: Building a faster, more streamlined Windows Search
Winsage
October 8, 2026

From searching to doing: Building a faster, more streamlined Windows Search

Search functionality is essential for navigating Windows PCs, and enhancements to the Windows Search Box were initiated in July to declutter the interface and improve user control. A new Windows Search experience powered by WinUI 3 will be available on the taskbar for Windows Insiders starting October 7, focusing on speed and efficiency with a streamlined design. The user interface has been simplified into a single list format, and improvements include better matching for typos and synonyms. Future updates will introduce inline previews, richer file details, and the ability to filter results. Inline actions will allow users to complete tasks directly from the search interface, such as toggling settings and managing their workspace. There are plans to integrate the new search experience into the Start menu and enhance its capabilities further. The new search experience is rolling out to Windows Insiders in the Experimental channel, with English as the initial supported language. Feedback can be shared through the Feedback Hub.
Windows 11 gains ground as price hike looms for Windows 10 security updates
Winsage
October 7, 2026

Windows 11 gains ground as price hike looms for Windows 10 security updates

Microsoft has extended its Windows 10 Extended Security Updates (ESU) program, allowing consumers to receive security updates at no cost until October 12, 2027. Businesses must pay to enroll, with a tiered pricing structure: the first year costs per device, the second year costs 2 per device, and the third year costs 4 per device. This price increase may encourage organizations to transition to Windows 11.
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