Windows Server 2025 Archives

Winsage

October 21, 2026

Windows Server 2025 gets support for quick machine recovery

Microsoft has introduced a Quick Machine Recovery (QMR) feature for IT administrators managing Windows Server 2025, enabling quick recovery from boot failures after the October 2026 security update without physical access to systems. When activated, QMR boots the system into the Windows Recovery Environment (WinRE) to troubleshoot issues, collecting crash data for remote assistance from Microsoft. Cloud remediation is disabled by default but can be enabled through Group Policy. Administrators can disable QMR by turning off 'Enable Cloud Remediation' and 'Enable Auto Remediation.' QMR was initially introduced in November 2024 as part of the Windows Resiliency Initiative and began testing in March 2025, with improvements made by November 2025.

Winsage

October 21, 2026

Windows Server 2025 Gets Support for Quick Machine Recovery

Windows Server 2025 introduced Quick Machine Recovery (QMR) in the October 2026 cumulative update to improve IT recovery processes during boot failures. QMR automates the detection of boot failures using the Windows Recovery Environment (WinRE) and can autonomously download and apply fixes via Windows Update. Organizations must manually enable QMR through Group Policy, as it is disabled by default. The feature enhances Windows Startup Repair with cloud-based remediation capabilities and requires a reliable network connection, supporting wired networks and WPA/WPA2 password-based Wi-Fi configurations.

Winsage

October 20, 2026

Microsoft Confirms October Windows Updates Can Break Exchange Server Email Services

Microsoft has acknowledged that the Windows Server security updates released on October 13, 2026, may disrupt Exchange Server email services, affecting on-premises systems running Exchange Server 2016, 2019, and the Subscription Edition. The disruptions can include blocked webmail access and undelivered messages. Microsoft has identified four specific Windows updates linked to these issues: KB5126646 for Windows Server 2025, KB5126655 for Windows Server 2022, KB5126651 for Windows Server 2019, and KB5126868 for Windows Server 2016. Symptoms may include inability to log into Outlook on the web, messages stuck in the Outbox, increased mail queues, and failed mailbox access. A critical error to monitor is MapiExceptionMdbOffline, and affected systems may log Event ID 1006. The October updates introduced a default limit of 512 simultaneous Endpoint Lookup calls, which can be exceeded under heavy Exchange workloads. Microsoft has provided a registry workaround to increase this limit and suggests monitoring for recurring failures. The disruption coincides with the end of the final paid update period for Exchange 2016 and 2019, with future updates limited to the Subscription Edition.

Winsage

October 16, 2026

Networking problems after the October 2026 Windows update? NTLM might be to blame

The Windows security update scheduled for October 2026 will block requests using the outdated NTLMv1 security protocol. The BlockNtlmSSO registry value governs this change; if unset, Windows will default to Enforce mode, blocking NTLMv1-derived credentials. Administrators can temporarily set this value to 0 to allow NTLMv1, but Microsoft warns this reduces security. The deprecation of NTLM was first announced in 2024, with audit logs for NTLMv1 usage introduced in August 2025. NTLM was first introduced in 1993, and while it has been removed from Windows 11 24H2 and Windows Server 2025, traces remain in certain configurations. Credential Guard must be enabled, and the BlockNtlmSSO value must not be set to Audit mode for NTLMv1-derived credentials to be allowed. Microsoft aims to eliminate NTLM entirely, and the upcoming update signals the need for organizations to accelerate their transition away from NTLMv1.

Winsage

October 15, 2026

Microsoft: Windows Server 2022 reached end of mainstream support

Windows Server 2022 has transitioned from mainstream support to extended support, which will last until October 2031. Mainstream support will end on October 13, 2026, with the last security update released in that month. Extended support will continue to provide essential security updates at no additional cost until October 14, 2031. Hotpatching for Windows Server 2022 will be available until October 2027 for Datacenter: Azure Edition. Microsoft recommends upgrading to Windows Server 2025, which will have mainstream support until November 2029 and extended support until November 14, 2034. Windows Server 2025 is set for general availability by November 2024. A free 180-day trial of Windows Server 2025 is available. Additionally, devices running Windows 11 24H2 Home and Pro editions will no longer receive updates, and users are advised to upgrade to Windows 11 26H2 to maintain security. Microsoft warns users of unsupported Windows versions to upgrade to avoid losing access to critical security updates after next year's Windows Update certificate rotation.

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.