Windows Server Archives

Winsage

June 29, 2026

Microsoft keeps Windows Server 2022 hotpatching alive into 2027

Microsoft has extended the availability of Windows Server 2022 hotpatching until 2027, specifically for the Windows Server 2022 Datacenter: Azure Edition. Mainstream support for Windows Server 2022 will end on October 13, 2026, while extended support will last until October 14, 2031. Hotpatching allows administrators to apply security updates without server downtime, although quarterly cumulative updates requiring a reboot will still occur. This feature is exclusive to Azure Edition users, with no similar support for on-premises users of Windows Server 2022. Additionally, hotpatch updates are being introduced for Windows 11 24H2 Enterprise clients and are now the default for Windows Autopatch.

Winsage

June 24, 2026

Windows 11 Bug Displays Internal Filenames in Recycle Bin

Microsoft is addressing a bug in Windows that affects the Recycle Bin functionality, where the confirmation prompt for permanently deleting files shows internal system filenames instead of the actual file names. This issue impacts all supported versions of Windows 11 and occurs when users attempt to delete files from the Recycle Bin. The Recycle Bin itself displays the correct file names, and file restoration works properly. The bug emerged after the June 9 Patch Tuesday updates and affects Windows 11 versions 23H2 through 26H1 and Windows Server versions from 2012 to 2025. Microsoft is working on a fix for this issue, which will be included in an upcoming update. Additionally, other issues have been reported following the updates, including problems with launching Office applications and stability issues like system crashes and BitLocker recovery prompts.

Winsage

June 19, 2026

Microsoft’s Patch Tuesday update strikes again

Microsoft has confirmed a bug affecting the Recycle Bin across all supported versions of Windows following its June 2026 Patch Tuesday update. The glitch causes the confirmation dialog to display an "internal" filename instead of the user-friendly filename when deleting files, although the actual file and its deletion process remain unaffected. The issue affects various Windows client and server versions, including Windows 11 (versions 26H1, 25H2, 24H2, 23H2), Windows 10 (versions 22H2, Enterprise LTSC 2021, Enterprise LTSC 2019, Enterprise LTSB 2016), and Windows Server (2025, 2022, 2019, 2016, 2012 R2, 2012). Microsoft is developing a permanent solution, but it is unclear when it will be released. Commercial customers can contact Microsoft Support for Business for a workaround.

Winsage

June 19, 2026

Microsoft’s latest Windows bug belongs in the Recycle Bin

Microsoft's recent Windows update has introduced a cosmetic glitch where the confirmation dialog for permanently deleting a file from the Recycle Bin displays the internal naming convention (e.g., $Rxxxxx.ext) instead of the original file name. This issue is limited to the deletion confirmation dialog; the original file name is preserved in the Recycle Bin and displayed correctly upon restoration. Microsoft has acknowledged the problem but has not provided a public workaround, advising organizations to contact Microsoft Support for assistance. A resolution is in progress and will be included in a future update. The glitch affects desktop versions of Windows from Windows 10 Enterprise LTSB 2016 to Windows 11 26H1, as well as Windows Server editions from 2012 to 2025.

Winsage

June 19, 2026

Microsoft confirms Recycle Bin bug across all versions of Windows

Reports have emerged about complications from the latest Patch Tuesday update, affecting users with issues such as access problems with OneDrive and Dropbox, BitLocker recovery lockouts, and Blue Screen of Death (BSOD) errors. Microsoft has acknowledged a glitch related to the Recycle Bin after the installation of June's Patch Tuesday update (KB5094126), where the confirmation dialog displays the internal file name instead of the actual name when deleting an item. This issue affects various supported Windows client and server versions, including Windows 11 (versions 26H1, 25H2, 24H2, 23H2), Windows 10 (versions 22H2, Enterprise LTSC 2021, Enterprise LTSC 2019, Enterprise LTSB 2016), and Windows Server (2025, 2022, 2019, 2016, 2012 R2, 2012). Microsoft is working on a solution expected in a future update, but it is unclear if it will be part of the next Patch Tuesday or an out-of-band update. Commercial customers can implement a workaround by contacting Microsoft Support for Business.

Winsage

June 18, 2026

Microsoft fixes Windows Server 2016 security update failures

Microsoft resolved an installation issue affecting the June 2026 security updates (KB5094122) on Windows Server 2016 systems that had not previously installed the KB5087537 update, which was a prerequisite. Users had encountered 0x80070002 or FILENOTFOUND errors. Microsoft acknowledged the problem and confirmed that affected devices should no longer experience installation failures for the June 2026 update. Additionally, Microsoft fixed a similar issue with the May 2026 Windows 11 security update (KB5089549) that resulted in 0x800f0922 errors due to insufficient space on the EFI System Partition. They also warned users about potential installation issues with error codes 0x80073712 or 0x800f0993 on devices upgraded to Windows 11 24H2 or 25H2. Furthermore, Microsoft addressed a boot issue for Windows Server 2025 devices after the April 2026 update and a bug affecting installation failures for updates since May 2025 using the Windows Update Standalone Installer (WUSA). Lastly, they are investigating a separate issue preventing third-party applications from launching essential Office programs after the June 2026 updates.

Winsage

June 14, 2026

Microsoft released Windows 11 KB5094149 / KB5095971 / KB5094156 Setup, Recovery updates

Microsoft released Patch Tuesday updates KB5094126 and KB5093998 for Windows 11, and KB5094127 for Windows 10. New Dynamic Update packages were introduced to enhance user experience by preserving Language Pack and Features on Demand content during upgrades. The updates include: - KB5095185: Safe OS Dynamic Update for Windows 11, version 26H1, improving WinRE to version 10.0.28000.2269. - KB5094149: Safe OS Dynamic Update for Windows 11, versions 24H2 and 25H2, enhancing WinRE to version 10.0.26100.8655. - KB5095971: Setup Dynamic Update for Windows 11, version 23H2, refining setup binaries for feature updates. - KB5094156: Safe OS Dynamic Update for Windows 11, version 23H2, improving WinRE to version 10.0.22621.7219. - KB5098815: Windows Recovery Environment update for Windows 10, versions 21H2 and 22H2, applying Safe OS Dynamic Update (KB5094154) to WinRE. - KB5094154: Safe OS Dynamic Update for Windows 10, versions 21H2 and 22H2, enhancing WinRE to version 10.0.19041.7417. - KB5094153: Safe OS Dynamic Update for Windows 10, version 1809 and Windows Server 2019, improving WinRE to version 10.0.17763.8880. - KB5094152: Safe OS Dynamic Update for Windows 10, version 1607 and Windows Server 2016, enhancing WinRE to version 10.0.14393.9234. These updates will be automatically downloaded and installed via the Windows Update channel.

Winsage

June 13, 2026

Windows Server is getting new network safety capabilities with DNS over HTTPS

Microsoft has introduced DNS over HTTPS (DoH) on Windows Server 2025, enhancing network security by encrypting DNS traffic for client-to-server communications. This feature, previously available only in Windows client editions, is now part of Microsoft's Zero Trust architecture. DoH routes DNS traffic through HTTPS secured with TLS certificates, preventing eavesdropping and safeguarding DNS data from tampering. It adheres to the IETF DNS over HTTPS standard (RFC 8484) and can integrate with existing infrastructure, allowing organizations to maintain unencrypted DNS traffic if needed. DoH is available for Windows Server 2025 systems updated to the latest Patch Tuesday release, and Microsoft has provided guidance on enabling this feature. However, DNS traffic exchanged between two DNS servers will not be encrypted by DoH.

Winsage

June 13, 2026

XP-era Windows spotted haunting London’s driverless railway

Commuters on London’s Docklands Light Railway (DLR) recently encountered an error message from the XP-era Windows operating system on an information screen, specifically from an application called DaisySignApp.exe. The display featured a Recycle Bin icon, indicating a nostalgic connection to Windows XP or Windows Server 2003, which lost support in 2015 and 2014, respectively. The DLR's digital display appears to be outdated, reflecting a reluctance to upgrade systems that are functioning adequately. Limehouse station, where the error was observed, connects the DLR to the UK’s National Rail services and has a history that predates Windows XP by over a decade. The DLR opened in 1987, during the launch of Windows 2.0.

Winsage

June 13, 2026

Windows Server 2025 Adds DNS Over HTTPS for Secure DNS Traffic

Microsoft has rolled out support for DNS over HTTPS (DoH) in Windows DNS Server as part of the Windows Server 2025 update. This feature enhances the security of DNS communications through encryption and server authentication, allowing encrypted client-to-resolver traffic in on-premises DNS environments. DoH encrypts DNS queries and responses using HTTPS, protecting sensitive information from interception or alteration. It also uses digital certificates for DNS server authentication to reduce spoofing and impersonation risks. The feature is compatible with existing Windows DNS Server configurations and supports both encrypted and traditional DNS. DoH support is available on Windows Server 2025 with the June 9, 2026 update or newer. Administrators must configure a trusted TLS certificate and enable DoH in the DNS Server service to deploy this feature. Microsoft plans to extend encryption capabilities to include communication between the Windows DNS Server and upstream DNS resolvers in the future.