Windows Server Updates Cause Remote Desktop Chaos

Recent Windows Server updates have been causing issues with Remote Desktop Services (RDS), leading to instability and connection failures. Microsoft has acknowledged the problem across multiple supported Windows Server versions, including Windows Server 2012 through Windows Server 2025.

The issue typically emerges hours after installing the September 2026 security updates, causing existing Remote Desktop sessions to hang, users to become unable to disconnect properly, and new connection attempts to frequently fail. In some environments, RDS might become unstable, resulting in RDP connections failing after several minutes or servers hanging during Remote Desktop configuration processes.

As a workaround, Microsoft recommends uninstalling the September 2026 updates on Windows Server machines, which would remove the security fixes delivered in the latest Patch Tuesday release. However, this also exposes the system to vulnerabilities.