Windows Server

Winsage
May 1, 2026
Microsoft resolved an issue affecting the display of security warnings when opening Remote Desktop (.rdp) files across all supported Windows versions, including Windows 11, Windows 10, and Windows Server. This problem was particularly evident on devices with multiple monitors having different display scaling settings. The fix was included in the optional KB5083631 preview cumulative update for Windows 11. The issue arose after the installation of the April 2026 security update, which introduced security warnings to enhance protection against phishing attacks. Users reported misalignment and obscured buttons in the security dialog, making it difficult to interact with. Additionally, the April security updates caused issues with third-party backup applications on Windows 11 systems and led to restart loops and failures during update installations on Windows Server.
Winsage
May 1, 2026
The KB5083769 security update released in April 2026 has disrupted the functionality of various third-party backup applications on Windows 11 versions 24H2 and 25H2, primarily due to issues with the Volume Shadow Copy Service (VSS). Affected applications include Acronis Cyber Protect Cloud, Macrium Reflect, NinjaOne Backup, and UrBackup Server. Users have reported receiving an error message indicating that backups have failed due to VSS timeouts. Acronis has acknowledged the issue, stating it affects both Windows 11 Pro and Home editions, and warns of potential broader system issues. A temporary solution involves uninstalling the KB5083769 update or pausing Windows updates. Additionally, Microsoft has issued out-of-band updates for critical issues affecting Windows Server systems and warned that some Windows Server 2025 devices may encounter BitLocker recovery prompts after installing the KB5082063 update.
Winsage
April 30, 2026
Attackers are exploiting CVE-2026-32202, a zero-click vulnerability in Windows Shell, allowing authentication of victims' systems without user interaction. This vulnerability stems from an incomplete patch for CVE-2026-21510 and has been used by the APT28 group with weaponized LNK files to bypass Windows security. Although Microsoft addressed these vulnerabilities in February 2026, the risk remains as opening a folder with a malicious LNK file can still connect victims' machines to the attacker's server, initiating an NTLM authentication handshake that exposes the victim’s Net-NTLMv2 hash. This affects various versions of Windows 10, 11, and Windows Server. Microsoft released a patch for CVE-2026-32202 on April 14, 2026, but did not label it as actively exploited until more than two weeks later, leaving security teams unaware of its urgency. Organizations are advised to apply the patch and consider blocking outbound SMB traffic to mitigate risks.
Winsage
April 28, 2026
Microsoft has identified an issue affecting the display of security warnings when users open Remote Desktop (.rdp) files across all supported versions of Windows, including Windows 11, Windows 10, and Windows Server. The security warning may not render correctly, making the text difficult to read and buttons misaligned, especially when multiple monitors with different display scaling settings are used. This issue often results in overlapping text or obscured buttons in the warning window. The problem is part of Microsoft's security enhancements introduced with the April 2026 cumulative updates, which aim to mitigate risks associated with malicious RDP connection files. Users receive a one-time educational prompt upon opening an RDP file for the first time, followed by a security dialog that provides information about the file's publisher and resource redirections. RDP files are commonly used in enterprise environments, but their exploitation in phishing campaigns has raised security concerns, particularly by groups like the Russian state-sponsored APT29.
Winsage
April 27, 2026
India’s cybersecurity agency, CERT-In, has issued an advisory regarding high-severity vulnerabilities in various Microsoft products, including multiple versions of Windows, Windows Server, Microsoft Office, and the Chromium-based Microsoft Edge browser. These vulnerabilities can allow attackers to execute malicious code, elevate system privileges, access sensitive data, or disrupt services. They arise from issues such as improper input validation, memory corruption, insufficient access control, and inadequate memory object handling. Exploitation can occur remotely or locally, sometimes requiring user interaction. CERT-In advises users and organizations to apply the latest security updates from Microsoft to mitigate these risks.
Winsage
April 23, 2026
The Competition Appeal Tribunal (CAT) has approved a £2 billion class action against Microsoft, aimed at compensating approximately 59,000 businesses using the Windows Server operating system in non-Microsoft public clouds. The collective action, led by Maria Luisa Stasi, alleges that Microsoft has overcharged UK entities for Windows Server on competing cloud services. The tribunal dismissed Microsoft's objections and granted a Collective Proceedings Order on an opt-out basis. The class action addresses two main issues: pricing abuse related to the Microsoft Service Provider License Agreement (SPLA) and re-licensing abuse concerning the deployment of Windows Server on Azure versus other cloud providers. The UK Competition and Markets Authority is also investigating Microsoft's software licensing practices within the cloud market. James Hain-Cole from law firm Scott+Scott expressed satisfaction with the tribunal's decision, emphasizing its significance for securing compensation for affected businesses.
Winsage
April 22, 2026
Microsoft is facing a £2 billion lawsuit in the UK, led by competition lawyer Maria Luisa Stasi, representing nearly 60,000 businesses that claim the company imposes excessive charges for using Windows Server on competing cloud platforms. The allegations focus on higher licensing fees for organizations using services like Amazon Web Services, Google Cloud Platform, and Alibaba Cloud compared to those using Microsoft’s Azure. The lawsuit has been allowed to proceed on an opt-out basis by the Tribunal. Microsoft plans to appeal the decision and asserts that its business model promotes competition. The case is part of broader scrutiny of Microsoft's licensing practices, with investigations also initiated by the UK Competition and Markets Authority and the European Commission, as well as inquiries in Brazil, Switzerland, the United States, and Japan.
Winsage
April 22, 2026
Support for Windows Server 2016 will officially end on January 12, 2027, ceasing security updates and bug fixes. Microsoft recommends upgrading to Windows Server 2019 or later to maintain support and security. Businesses are advised to assess their IT infrastructure and develop a migration strategy to ensure continuity and security. Engaging with IT professionals is recommended for managing the transition effectively.
Winsage
April 21, 2026
Microsoft has released an out-of-band update to fix a restart loop issue affecting certain Windows Server devices after the April 2026 update. The problem arose after installing the April 2026 Windows security update (KB5082063), causing domain controllers in multi-domain environments using Privileged Access Management (PAM) to experience LSASS crashes during startup, leading to repeated restarts and potential domain outages. The update targets Windows Server versions 2016 through 2025 and includes hotpatches for failed installations. Only Windows Servers were affected, while some enterprise devices may need to enter their BitLocker recovery key after the first restart post-installation. Microsoft has issued similar updates recently, raising concerns about the frequency of these occurrences.
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