Windows Server Update Services

Winsage
October 11, 2026
Windows machines that are not current with updates will face changes in access to Windows Update due to two critical certificate expirations on May 17, 2027, and June 19, 2027. Supported versions must install specific security updates before these dates to maintain access. - Windows 11, version 25H2 and later: No action required. - Windows 11, version 24H2 and Windows Server 2025: Must install the September 2025 Windows security update or later, before June 19, 2027. - Other in-support Windows 11 versions and Windows Server 2022: Must install the July 2026 Windows security update or later, before June 19, 2027. - In-support Windows 10 versions: Must install the July 2026 Windows security update or later, before June 19, 2027. - Windows 10 Enterprise 2019 LTSC, Windows Server 2019, and Windows Server 2016: Must install the July 2026 Windows security update or later, before May 17, 2027. - Any other Windows version: Upgrade to a supported release to maintain access. Devices that are up to date will continue receiving updates without interruption, while those that are behind will lose access to Windows Update services after the expiration dates. Out-of-support versions will lose access entirely. The notice regarding the certificate expiration was posted on October 8, 2026, and reiterated on October 10, 2026.
Winsage
October 9, 2026
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.
Winsage
August 28, 2026
Microsoft has released Windows 11 version 26H2 (Build 26300.9278) in the Release Preview Channel for customers to preview ahead of its general availability later this year. This version will be delivered as an enablement package, allowing for seamless integration of new features and enhancements. Users with PCs in the Release Preview channel can manually install this version. Key features for business users include Windows Backup, app actions from the Taskbar, and improvements to File Explorer. Organizations can deploy Windows 11 version 26H2 using Windows Update client policies and Windows Server Update Services (WSUS). Updates to the ISOs on the Windows Insider Program download site will also reflect this new version.
Winsage
August 10, 2026
Microsoft is offering Extended Security Updates (ESUs) for Windows Server 2016, which will provide critical security patches until January 2030, after the end of extended support on January 12, 2027. Organizations can enroll their Windows Server 2016 instances via Azure Arc to receive these updates without migrating to Azure. The ESUs are available through a pay-as-you-go pricing model, allowing flexibility for on-premises servers and other cloud platforms. By using Azure Arc, organizations gain access to Azure management tools for improved visibility and compliance. IT administrators should connect eligible systems to Azure Arc to manage ESU enrollment and compliance effectively. ESUs are intended as a temporary solution while businesses modernize applications and plan migrations to supported platforms.
Winsage
July 24, 2026
This week, Meta experienced a global outage affecting Facebook users, followed by Microsoft facing performance issues with its M365 services, including Teams and SharePoint. Microsoft also reported difficulties with Azure, impacting Windows 11 updates and the Microsoft Store. The issues began around 11:15 AM PST on July 23, 2026, with a notification to users about the Azure outage affecting Windows Update and related services. Microsoft initiated recovery efforts and by 1:45 PM PST, announced that the issues were resolved and services were restored. Currently, there are no ongoing issues reported on the Microsoft Service Health Status page, but the incident is documented on the Windows Release Health page.
Winsage
July 13, 2026
Microsoft has released a guide on the Windows servicing model, detailing monthly security updates, optional preview releases, hotpatch updates, and feature rollout mechanisms. Patch Tuesday occurs every second Tuesday of the month, delivering cumulative security updates to supported Windows versions. For consumers and small businesses, updates are managed through Windows Update, while enterprises can use various tools like Windows Autopatch and WSUS. Hotpatch updates, which focus on security fixes, can be installed without a restart, unlike quarterly baseline updates that require one. Optional non-security preview updates are released in the fourth week of each month for testing upcoming fixes and new features, available only for the latest supported Windows versions. Unmanaged devices can access these updates through Windows Update settings, while IT-managed devices depend on organizational policies. Microsoft also issues out-of-band updates to address urgent issues, which can be deployed through enterprise management tools. New features for Windows 11 are rolled out throughout the year via various channels, with a gradual rollout strategy to monitor quality and compatibility, using the Controlled Feature Rollout approach.
Search