Server 2025 Archives

Winsage

October 11, 2026

Windows PCs that are not up to date will lose Windows Update itself in 2027

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Microsoft: Outdated Windows devices will stop receiving security updates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.

Winsage

September 25, 2026

Microsoft plans to deprecate Windows Deployment Services

Microsoft has announced that Windows Deployment Services (WDS) will be deprecated in the upcoming Windows Server release, marking a significant change for IT administrators who have used WDS for remote Windows installations. Active development of WDS will cease after the next Windows Server version, and the service will eventually be retired. This follows previous deprecations, including the removal of boot.wim support in 2021 and the disabling of hands-free deployment in January 2026 for certain updates. WDS will continue to operate on currently supported Windows Server versions, but standard desktop operating systems are no longer supported through its native setup engine since Windows 11. The deprecation includes the entire WDS ecosystem, but Microsoft Configuration Manager's deployment capabilities will remain unaffected. Users are encouraged to plan their migration away from WDS dependencies.

Winsage

September 19, 2026

Microsoft fixes bug behind ‘Defender Antivirus is turned off’ alerts

Microsoft resolved an issue that caused misleading alerts indicating that Defender Antivirus was disabled after recent updates. This fix was confirmed in an update to the Windows release health dashboard and was implemented in the Microsoft Defender Antivirus update (version 4.18.26080.4) rolled out on September 17. The bug, acknowledged by Microsoft in late August, affected users in the Release Preview Channel of the Windows Insider program since at least June and impacted all supported versions of Windows clients and servers. Users received erroneous notifications in the Windows Security app prompting them to activate Microsoft Defender Antivirus, despite it functioning correctly. Misleading alerts could appear upon Windows startup and intermittently thereafter, even when notification settings were disabled.

Winsage

September 18, 2026

Windows 11 Update Can Break Active Directory Trust Relationships

A recent security update from Microsoft, KB5124008, has caused disruptions for organizations using on-premises Active Directory, particularly affecting domain-joined Windows 11 devices with Credential Guard. After installing this update, some devices lost their secure trust relationship with the domain, preventing users from logging in with valid credentials. The issue is linked to Machine Identity Isolation, a security feature that enhances machine account credential protection but requires domain controllers to operate at the Windows Server 2025 Domain Functional Level. Organizations that enabled this feature without meeting the prerequisite may experience trust relationship failures. Microsoft has suggested a workaround to disable Machine Identity Isolation and plans to suspend its enforcement in an upcoming update while improvements are made.

Winsage

September 17, 2026

Microsoft patch gives domain-joined Windows PCs trust issues

Microsoft acknowledged a significant issue affecting Windows 11 versions 24H2, 25H2, and 26H1 related to Active Directory domain logins as of September 16. This issue stems from changes made to Machine Identity Isolation in the September 2026 security update (KB5124008), which may cause Credential Guard-protected machine accounts to lose their secure channel with an on-premises Active Directory domain, preventing users from signing in with valid domain credentials. The update activates Machine Identity Isolation but does not enforce it immediately, and it is only compatible with environments linked to domain controllers operating at the Windows Server 2025 Domain Functional Level (DFL) or higher. Microsoft advised that devices not connected to Windows Server 2025 domain controllers will need to disable Machine Identity Isolation. A workaround involves disabling the feature through Intune, Group Policy, or the Windows Registry, followed by a device restart and repairing the secure channel using the Test-ComputerSecureChannel PowerShell command. Microsoft plans to address this issue in a future update by temporarily halting Machine Identity Isolation enforcement while enhancements are made.

Winsage

September 16, 2026

Windows Server 2022 Nears End of Mainstream Support

Organizations using Windows Server 2022 will lose mainstream support on October 13, 2026, although security updates will continue through extended support until October 2031. Customers are encouraged to plan for an upgrade to Windows Server 2025 to avoid potential security vulnerabilities and complications in future migrations. Microsoft recommends early evaluation and testing of Windows Server 2025 to ensure compatibility and smooth transition. Additionally, support for the Azure Edition’s hotpatching capability has been extended to October 2027, providing some customers more time to strategize their migration. However, remaining on Windows Server 2022 means missing out on new features and enhancements.

Winsage

September 16, 2026

Windows Server 2022 reaches end of mainstream support next month

Microsoft has announced that mainstream support for Windows Server 2022 will end next month, transitioning to an extended support phase that lasts until October 2031. Windows Server 2022 was released in September 2021 and will receive its final mainstream support update on October 13, 2026. After this date, it will continue to receive essential security updates at no extra cost until October 14, 2031. Hotpatching for Windows Server 2022 will be available until October 2027 for Datacenter: Azure Edition. Microsoft encourages administrators to upgrade to Windows Server 2025, which began rolling out to Windows Insiders in January 2024 and is expected to be generally available by November 2024. Windows Server 2025 will have mainstream support until November 13, 2029, followed by five years of extended support until November 14, 2034. A 180-day trial of Windows Server 2025 is available through the Microsoft Evaluation Center.

Winsage

September 15, 2026

Microsoft issues emergency Windows 11 update to fix its record-breaking patch

Microsoft has rolled out an emergency out-of-band update to address issues from its September Patch Tuesday update, which affected nearly 1,000 vulnerabilities and caused bugs in folder shares on Hyper-V-based Linux virtual machines, Remote Desktop Services sessions, and certain USB audio devices. The new update targets multiple versions of Windows 11 (26h1, 25H2, and 24H2) and also includes updates for Windows Server 2025, 2022, and LTSC versions of Windows 10 and Windows Server 2012 and 2012 R2. In 2023, Microsoft has increasingly issued out-of-band updates, including four in January, two in March, and one in July, to resolve various issues.

Winsage

September 14, 2026

Latest Windows Server Updates Cause Remote Desktop Issues

Organizations that implemented Microsoft’s September 2026 security updates are experiencing challenges with Remote Desktop Services (RDS) on Windows Server systems, leading to instability and connection failures. Issues typically arise hours after the update, causing ongoing Remote Desktop sessions to freeze, difficulties in disconnecting, and failures in establishing new connections. Affected systems include Windows Server 2012 through Windows Server 2025 and select Windows client versions, with problems such as failed RDP connections, sign-in difficulties, unresponsive management tools, and servers stalling during Remote Desktop configuration. Microsoft advises administrators to uninstall the September 2026 updates, which would remove security enhancements, and is investigating the root cause while providing Known Issue Rollback policies. For inaccessible virtual machines, restarting the affected VM is recommended as a temporary measure.