Server 2025

Winsage
June 12, 2026
Microsoft resolved an issue affecting the installation of Windows updates released since May 2025, which primarily impacted users using the Windows Update Standalone Installer (WUSA) from a network share, especially in enterprise environments. The problem was significant for devices running Windows 11 24H2/25H2 and Windows Server 2025, but did not occur when handling a single .msu file or when files were stored locally. In August 2025, Microsoft acknowledged that updates installed using WUSA might fail with error ERRORBADPATHNAME when multiple .msu files were involved. A Known Issue Rollback Group Policy was implemented in September 2025 to mitigate the impact on home and non-managed business devices. The issue was ultimately resolved with cumulative updates released in June 2026 for Windows 11 (KB5079391) and Windows Server 2025 (KB5094125). Microsoft provided a workaround for users experiencing difficulties with prior updates by suggesting they save .msu files locally for installation. Users were also advised to wait at least 15 minutes after installing an .msu file via WUSA before checking the Update History page. Additionally, Microsoft had previously addressed another issue in April 2025 that affected enterprise customers installing security updates via WSUS, which recurred in the August 2025 updates. Microsoft warned customers about potential issues with installing the latest monthly updates on devices upgraded to Windows 11 24H2 or 25H2.
Winsage
June 11, 2026
Microsoft has resolved an issue affecting certain Windows Server 2025 devices that were booting into BitLocker recovery mode after the April 2026 security update. This issue was linked to specific BitLocker Group Policy configurations and required users to input their BitLocker recovery key upon the first restart after the update. However, this key would only need to be entered once for subsequent restarts, provided the group policy configuration remained unchanged. The problem primarily affected enterprise systems rather than personal devices. The issue arose under specific conditions: BitLocker was enabled on the operating system drive, a particular Group Policy was set, the Secure Boot State PCR7 Binding was "Not Possible," the Windows UEFI CA 2023 certificate was present, and the device was not already using the 2023-signed Windows Boot Manager. Microsoft released fixes in the KB5094125 and KB5093998 updates to address this problem, preventing devices with incompatible group policy configurations from installing the 2023-signed Windows Boot Manager. Event ID 1032 in the System event log indicates the issue when Windows updates are installed. For IT administrators unable to deploy the latest updates, it is recommended to remove the Group Policy configuration before installing updates or to implement a Known Issue Rollback (KIR) on affected devices. Additionally, Microsoft had previously addressed similar BitLocker recovery issues in August 2024 and May 2025.
Winsage
June 10, 2026
On June 9, 2026, Microsoft announced a vulnerability in Windows BitLocker, identified as CVE-2026-50507, which allows unauthorized attackers with physical access to bypass BitLocker Device Encryption. The flaw is categorized under CWE‑306, indicating a missing authentication check for a critical function, and has a CVSS v3.1 base score of 6.8. It affects various versions of Windows 10, Windows 11, and Windows Server from 2012 R2 to 2025. Microsoft released security updates to address the vulnerability, and it was classified as “Exploitation More Likely.” Although there is no evidence of active exploitation, proof-of-concept code exists. Organizations are advised to implement multi-factor configurations and reassess device handling and security protocols.
Winsage
June 8, 2026
Microsoft has rolled out new Defender patches for Windows 11 ISOs, aligning with its commitment to security updates. Updates for Microsoft Defender for Endpoint's endpoint detection and response (EDR) will no longer be included with monthly Windows security updates or Patch Tuesdays; they will now be delivered via Microsoft Update. This change aims to allow faster deployment of EDR enhancements independently of the operating system's update cycle. The rollout for Windows 10 began in late May 2026, with plans to extend support to Windows 11 and other versions by fall 2026. EDR updates will be delivered using KB5005292, contingent on prerequisite updates. Systems must run Sense version 10.8798.25857.1000 or later and have specific Windows updates installed to qualify for the new delivery method. Organizations should align their update policies with this new approach before the broader rollout. In case of significant issues, the EDR update can be reverted using a specific command. Further details are available in the Microsoft 365 Admin Center under message ID MC1381119.
Winsage
May 28, 2026
Microsoft has acknowledged an issue with the May 2026 security update for Windows Server 2016, affecting systems with hostnames of exactly 15 characters, which leads to failed domain controller (DC) lookups. The error occurs during DC lookups, specifically returning the error code ERRORINVALIDPARAMETER. Servers with 14 or 16 character hostnames are not affected. Administrators may face challenges with DFS Namespace management and other functions reliant on DC access. Microsoft is investigating the issue but has not provided a timeline for a fix. Windows Server 2016's mainstream support ended in January 2022, but extended support will continue until January 2027.
Winsage
May 26, 2026
Microsoft has acknowledged an issue affecting Windows Server 2016 systems related to domain controller lookups after the installation of the KB5087537 security update released in May 2026. The problem occurs specifically for devices with hostnames that are exactly 15 characters long, causing domain controller discovery to fail and resulting in an ERRORINVALIDPARAMETER during DCLocator calls. This issue may disrupt administrative operations that depend on domain controller lookups, such as DFS Namespace management. Microsoft is investigating the issue but has not provided a timeline for resolution.
Winsage
May 23, 2026
BitLocker, a security feature for data protection, has a vulnerability identified as CVE-2026-45585, also known as YellowKey, which allows unauthorized access to encrypted data on Windows 11 versions 24H2, 25H2, 26H1, and Windows Server 2025. This flaw does not compromise BitLocker’s encryption but affects the recovery environment supporting it. The vulnerability can be exploited locally through the Windows Recovery Environment (WinRE) by an attacker with physical access, who can trigger an unrestricted shell and access the BitLocker-protected volume. Microsoft has provided two mitigation strategies: modifying the WinRE image to remove the autofstx.exe entry and transitioning from TPM-only protection to a TPM+PIN requirement at startup. The exploit poses challenges for detection, as it occurs pre-boot and currently lacks vendor-published indicators of compromise. Organizations using BitLocker for unattended devices are particularly at risk, as the vulnerability can lead to loss of confidentiality if an attacker gains access before the legitimate user.
Winsage
May 21, 2026
A segment of Windows 11 users has been unable to receive updates since February due to issues stemming from the January Preview Update, which caused download timeouts. This has resulted in missed security patches and critical updates related to Secure Boot certificates. Users may experience crashes during the update process, indicated by the error code 0x80010002. To check if affected, users can view their update history in Settings; if no updates have been installed since January and updates have not been paused, they are likely impacted. Microsoft is working on a fix linked to download timeout changes and firewall settings. A Known-Issue Rollback (KIR) can be executed to revert to a previous state before the problematic update, restoring normal functionality. This rollback is available for specific Windows 11 versions and Windows Server 2025.
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