Windows Server 2025 known issues

Microsoft lists 1 open issue for Windows Server 2025. Below is every issue Microsoft has listed for this version, with the update that caused it and when it was resolved.

IssueStatusCaused byOpenedResolved or updated
SQL Server linked server connections might remain openConfirmedOS Build 26100.33650, KB5126646, 2026-10-1311 November 202611 November 2026
Users might be unable to sign in to OWA or send emails on Exchange ServerResolved KB5131080OS Build 26100.33650, KB5126646, 2026-10-1310 November 202610 November 2026
USB audio devices might fail to start or produce no soundResolved KB5131080OS Build 26100.33438, KB5122871, 2026-09-0810 November 202610 November 2026
Remote Desktop Services might stop responding after Sept. 2026 security updateResolved KB5129235OS Build 26100.33438, KB5122871, 2026-09-0811 September 202614 September 2026
Incorrect notifications that "Microsoft Defender Antivirus is turned off"ResolvedN/A28 August 202630 September 2026
Windows Server Update Services sync operations might have issues or time outResolvedN/A18 July 202620 July 2026
GIF functionality in the Windows Emoji Panel might become unavailableResolved KB5120233N/A30 June 202611 August 2026
Deleting a file from the Recycle Bin displays an internal filename in the dialogResolved KB5099536OS Build 26100.32995, KB5094125, 2026-06-0918 June 202614 July 2026
Domain controllers may restart repeatedly after installing April security updateResolved KB5091157OS Build 26100.32690, KB5082063, 2026-04-1417 April 202619 April 2026
Apps might become unresponsive when saving files to cloud-backed storageResolved KB5078135OS Build 26100.32230, KB5073379, 2026-01-1321 January 202623 January 2026
Connection and authentication failures in Azure Virtual Desktop and Windows 365Resolved KB5077793OS Build 26100.32230, KB5073379, 2026-01-1314 January 202617 January 2026
USB mouse and keyboard not working in the Windows Recovery Environment (WinRE)Resolved KB5070773OS Build 26100.6899, KB5066835, 2025-10-1418 October 202520 October 2025
Smartcard authentication issues might occur with the October 2025 Windows updateResolvedOS Build 26100.6899, KB5066835, 2025-10-1418 October 202523 October 2025
IIS websites might fail to loadResolved KB5068861OS Build 26100.6899, KB5066835, 2025-10-1416 October 202511 November 2025
Directory synchronization fails for AD groups exceeding 10,000 membersResolved KB5068861OS Build 26100.6584, KB5065426, 2025-09-0915 October 202511 November 2025
Updates installed via WUSA might fail if installed from a shared folderResolved KB5094125OS Build 26100.4349, KB5060842, 2025-06-1015 August 20259 June 2026
Windows Server 2022 and Server 2019 unexpectedly upgraded to Windows Server 2025Resolved KB5082063N/A9 November 202414 April 2026

Source: Microsoft's release health page for Windows Server 2025. Dates are in UTC.

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