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‘Fail To Shut Down’—Microsoft Issues Windows Update Warning
Winsage
January 16, 2026

‘Fail To Shut Down’—Microsoft Issues Windows Update Warning

Microsoft has raised concerns about the shutdown process of Windows PCs, indicating complications following the January 13, 2026, security update. PCs with Secure Launch may fail to shut down or hibernate, instead restarting unexpectedly. A temporary solution is to use the Command Prompt with the command shutdown /s /t 0 for shutting down, but there is no workaround for the hibernation issue. Microsoft recommends saving work and shutting down devices to avoid power loss. Additionally, some users are facing credential prompt failures during Remote Desktop connections, affecting services like Azure Virtual Desktop and Windows 365. Alternatives include using the Remote Desktop client for Windows or the Windows App Web Client. An emergency update is expected to resolve these issues.
Microsoft Ends Windows Server 2008 Support on January 13, 2026
Winsage
January 16, 2026

Microsoft Ends Windows Server 2008 Support on January 13, 2026

Microsoft has officially ceased all support for Windows Server 2008 as of January 13, 2026, including paid extended security updates. This end-of-life scenario poses significant security risks for organizations still using the outdated operating system, making them vulnerable to cyberattacks. The transition away from Windows Server 2008 requires careful planning, as many organizations face challenges in migrating legacy applications to modern systems. The lack of ongoing patches means that any new vulnerabilities will remain unaddressed, potentially leading to data breaches and compliance failures, particularly in regulated sectors like healthcare and finance. Microsoft has encouraged migration to Azure, offering incentives for early adopters, but the transition can be complex and costly. The end of support also affects global supply chains and compatibility with newer software applications. Organizations are advised to conduct audits of their software portfolios and consider hybrid environments to enhance flexibility and security.
Windows Server 2008 is finally gone, after Microsoft pulls support at last
Winsage
January 15, 2026

Windows Server 2008 is finally gone, after Microsoft pulls support at last

Microsoft concluded all support for Windows Vista and Server 2008 as of January 13, 2026. Most customers lost support in January 2020, but Extended Security Updates were available until January 2023 for most users and until January 2024 for Azure customers. Free security updates, non-security updates, and support options are no longer accessible for the retired codebase. Organizations are encouraged to migrate to Azure for additional security updates. Windows Server 2012 will also reach the end of its ESU on October 13, 2026.
Windows App forgets how to log in with first security update of the year
Winsage
January 15, 2026

Windows App forgets how to log in with first security update of the year

Microsoft's January security update, released on January 13, 2026, has caused connection and authentication failures for users of Azure Virtual Desktop and Windows 365, particularly affecting those using the Windows App. The update has resulted in credential prompt failures during Remote Desktop connections across all supported Windows versions, from Enterprise LTSC 2016 to Windows 11 25H2, as well as Windows Servers from 2019 to 2025. Microsoft is investigating the issue and plans to release an out-of-band update soon. Users have been advised to either uninstall the update or use the Remote Desktop Client or the Windows App web client as workarounds. Reports indicate persistent issues, including an "Unable to Authenticate" error when attempting to connect via the Windows App. Microsoft has also made a Known Issue Rollback available to address these credential problems.
U.S. CISA adds a flaw in Microsoft Windows to its Known Exploited Vulnerabilities catalog
Winsage
January 14, 2026

U.S. CISA adds a flaw in Microsoft Windows to its Known Exploited Vulnerabilities catalog

The U.S. Cybersecurity and Infrastructure Security Agency (CISA) has added a Microsoft Windows vulnerability, CVE-2026-20805, to its Known Exploited Vulnerabilities (KEV) catalog, with a CVSS score of 8.7. This vulnerability, part of the January 2026 Patch Tuesday updates, affects the Windows Desktop Window Manager and allows attackers to leak memory information, potentially aiding in further exploits. Federal Civilian Executive Branch agencies must address this vulnerability by February 3, 2026, as mandated by Binding Operational Directive 22-01.
Microsoft fixes 114 flaws in year's first Windows 11 Patch Tuesday
Winsage
January 13, 2026

Microsoft fixes 114 flaws in year’s first Windows 11 Patch Tuesday

Microsoft's January 2026 Patch Tuesday update, KB5074109, addresses 114 vulnerabilities, including a critical zero-day vulnerability (CVE-2026-20805) in the Windows Desktop Window Manager (DWM) that has been actively exploited. The update is applicable to Windows 11 versions 24H2 and 25H2 and includes security enhancements and updates to AI components. Other high-severity vulnerabilities addressed include CVE-2026-20816 (privilege escalation in Windows Installer), CVE-2026-20817 (elevation of privilege in Windows Error Reporting), CVE-2026-20840 (vulnerability in Windows NTFS), CVE-2026-20843 (flaw in Routing and Remote Access Service), CVE-2026-20860 (vulnerability in Ancillary Function Driver for WinSock), and CVE-2026-20871 (another DWM vulnerability). The update removes legacy modem drivers to minimize the attack surface and resolves reliability issues in Azure Virtual Desktop and WSL networking. It also changes the default setting for Windows Deployment Services (WDS) to disable hands-free deployment. Users can install the update through Windows Update, and a system reboot is required for full application.
Microsoft Tests Uninstall Option for Copilot AI on Windows Devices
Winsage
January 11, 2026

Microsoft Tests Uninstall Option for Copilot AI on Windows Devices

Microsoft is testing a new policy that allows IT administrators to completely uninstall its Copilot AI assistant from managed Windows devices. This policy, named “RemoveMicrosoftCopilotApp,” is being deployed through management tools like Intune and System Center Configuration Manager (SCCM) and addresses concerns about data privacy, resource consumption, and unwanted software in commercial settings. The feature is currently available in Windows 11 Insider Preview Build 26220.7535 (KB5072046) and reflects feedback from IT professionals who prefer controlled environments. While this option is exclusive to enterprise-tier Microsoft 365 subscribers, smaller businesses and individual users have limited options for removal. The policy aims to balance innovation with risk management, especially in regulated sectors like healthcare and finance, where data privacy is critical.
Microsoft Ends Windows 11 SE Support in 2026 Amid Low Adoption
Winsage
January 5, 2026

Microsoft Ends Windows 11 SE Support in 2026 Amid Low Adoption

Microsoft will conclude support for Windows 11 SE in 2026, ceasing security updates and feature enhancements after October 2026. Launched in late 2021 for K-8 classrooms, Windows 11 SE struggled with adoption due to hardware limitations and competition from alternatives like Google’s Chrome OS. The final feature release for SE will be Windows 11 version 24H2. Schools will face challenges in transitioning to new systems, as devices running SE may become vulnerable to cyber threats without ongoing support. Microsoft is shifting its focus to integrating educational tools into its main operating system rather than maintaining a separate edition. The end of support for Windows 11 SE may accelerate hardware refresh cycles in schools, posing financial burdens on underfunded districts.
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