Organizations that implemented Microsoft’s September 2026 security updates are experiencing challenges with Remote Desktop Services (RDS) on Windows Server systems, leading to instability and connection failures. Issues typically arise hours after the update, causing ongoing Remote Desktop sessions to freeze, difficulties in disconnecting, and failures in establishing new connections. Affected systems include Windows Server 2012 through Windows Server 2025 and select Windows client versions, with problems such as failed RDP connections, sign-in difficulties, unresponsive management tools, and servers stalling during Remote Desktop configuration. Microsoft advises administrators to uninstall the September 2026 updates, which would remove security enhancements, and is investigating the root cause while providing Known Issue Rollback policies. For inaccessible virtual machines, restarting the affected VM is recommended as a temporary measure.