Windows Server

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
October 5, 2026
Microsoft is enhancing Intune and Configuration Manager to support the transition to Windows 11 version 26H2 for enterprise administrators. Intune now offers day zero support for Windows 11 version 26H2 settings, allowing IT administrators to configure new Windows policies through the Intune admin center. An updated security baseline for Windows 11 version 26H2 will also be released. Configuration Manager versions 2603 and 2609 support Windows 11 version 26H2, providing platform enhancements and updated security controls. IT teams are advised to review new settings, test on representative devices, ensure OS compatibility, and monitor deployments. Organizations using Configuration Manager may need to upgrade their environments and address the discontinuation of support for older platforms like Windows Server 2012/2012 R2 and SQL Server 2016.
Winsage
October 2, 2026
Talee helps businesses utilize Microsoft's technology ecosystem, which includes Windows, Microsoft 365, Azure, SQL Server, Visual Studio, security, and artificial intelligence. The company integrates these tools into cohesive solutions for organizations undergoing digital transformation. Talee emphasizes the interconnectedness of Microsoft's offerings, enabling organizations to leverage technologies like Microsoft 365, Azure, and AI tools effectively. The modern workplace has evolved with Microsoft 365 integrating productivity applications with cloud storage and collaboration tools. Talee supports the transition from traditional desktop computing to cloud infrastructure using Microsoft Azure. It also connects Microsoft SQL Server and Azure for data management. AI is increasingly embedded in Microsoft's ecosystem, enhancing user interactions with software. Talee's solutions cater to both end-users and developers, utilizing tools like Visual Studio and Azure. Security is a critical focus, with Microsoft providing comprehensive security measures across its ecosystem. Talee promotes viewing Microsoft's technology portfolio as an interconnected ecosystem rather than isolated products, facilitating organizations' ability to adapt to future technological needs.
Winsage
September 25, 2026
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 25, 2026
Microsoft has acknowledged an issue affecting some Windows 11 users utilizing virtual desktops, where a black screen appears after sign-in, requiring manual launch of Explorer to regain access. This glitch is linked to devices operating on the August 2026 non-security preview update or later. It has been predominantly observed on Azure Virtual Desktop (AVD) hosts using FSLogix, with crashes of Windows Explorer noted in the Application event log. A temporary workaround involves using Task Manager to initiate explorer.exe as a new task. Microsoft has implemented a Known Issue Rollback (KIR) via Group Policy to disable the problematic change until a permanent fix is released. Versions 26H1, 25H2, and 24H2 of Windows 11 are affected, while Windows 10 and Windows Server do not appear to be impacted.
Tech Optimizer
September 24, 2026
A small business is typically defined as one where the owner can personally name all employees, usually comprising a workforce of a few dozen. Licensing options for IT protection for small businesses vary, with Malwarebytes and Norton covering up to 20 devices, ESET offering plans for five to 25 devices, and Bitdefender providing options for three, five, ten, or 25 users. Avast and AVG allow licenses for one to 999 devices. All security suites support Windows, and most, except AVG, also support Mac devices. Four suites offer protection for Android and iOS devices, while Avast and AVG do not support mobile devices. Bitdefender, ESET, and Norton provide dedicated server editions, while Avast and AVG allow individual policy definitions for servers. Remote installation features vary in reliability, but all suites enable administrators to manage installations and monitor device status. Norton offers backup solutions and 500GB of shared hosted storage, while firewall protection is standard except for Malwarebytes. Bitdefender and ESET provide anti-theft systems for lost devices, and both ESET and Avast have measures against unauthorized device access. Malwarebytes and Norton offer 24/7 priority support, and Norton provides dark web monitoring for sensitive information.
Winsage
September 22, 2026
Changing the desktop wallpaper to a solid color in Windows 7 caused a 30-second delay on the Welcome screen after entering a password. This issue arose because the system waited for a signal from the wallpaper component, which only sent its "I'm ready" signal when an image file was used. When a solid color was selected, this signal was not sent, leading to unnecessary waiting. The problem was acknowledged by Microsoft for both Windows 7 and Windows Server 2008 R2, and it was resolved with a Hotfix update in November 2009. Users found workarounds, such as switching to an image or creating a small solid-color image, to eliminate the delay.
Winsage
September 20, 2026
Microsoft resolved an issue in its Windows Security framework that incorrectly indicated Microsoft Defender Antivirus was disabled. This fix was implemented through Defender platform update 4.18.26080.4, released on September 17. The update installs automatically unless users have blocked mandatory security updates. Users had been receiving false alerts during system boot and intermittently afterward, which redirected them to the Windows Security home tab where settings appeared normal. Microsoft acknowledged the issue on August 28, affecting all supported versions of Windows and Windows Server with the latest Defender updates, but did not specify the triggering update. Users in the Windows Insider program reported similar warnings as early as June.
Tech Optimizer
September 19, 2026
For nearly two months, Windows 11 users received persistent notifications from the Windows Security app falsely indicating that Microsoft Defender was disabled, despite it functioning properly. This issue, which began in early August, has been addressed with a security update from Microsoft. The false alerts affected all versions of Windows 11, Windows Server, and Windows 10, and were linked to a bug introduced with a recent Defender security update. Microsoft confirmed that no manual action is required from users to resolve the issue, as the fix will be automatically deployed to all PCs with mandatory security updates enabled. The problem was resolved in the Microsoft Defender Antivirus update (version 4.18.26080.4), released on September 17, 2026. Users can verify the status of Defender by checking Windows Security or using a PowerShell command.
Winsage
September 19, 2026
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.
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