Microsoft’s September 2026 Patch Tuesday delivered nearly 1,000 vulnerability fixes, including two actively exploited flaws. Unfortunately, the security updates also triggered widespread Remote Desktop Services failures across Windows Server 2012 through 2025, as well as Windows 10 and 11. Noel Bradford dissects the uncomfortable trade-off administrators now face: leave the patch installed and risk breaking production RDS environments, or remove it and deliberately reinstate known security holes. Microsoft’s current mitigation, stopping and restarting affected servers, highlights the absurdity of the situation. This episode examines what went wrong in testing, why patching remains essential despite these failures, and how organisations can build deployment rings and monitoring that prevent turning users into the first line of incident detection. If your patch strategy is ‘deploy everything at once’, you are not managing risk. You are gambling with availability.

• Cold Open A Monday morning scenario: servers patched on schedule, compliance dashboards green, yet Remote Desktop sessions are dropping everywhere. Users cannot sign in, management tools freeze, and the security update that caused the chaos also fixes vulnerabilities attackers are already exploiting. The choice becomes: break the system or reinstall known security holes.
• But You Cannot Just Rip The Patch Out September 2026 marks Microsoft’s largest Patch Tuesday on record, with approximately 966 to 970 vulnerabilities addressed. Two were already being actively exploited. Uninstalling the update to restore RDS functionality means deliberately reinstalling vulnerabilities under active attack. There is no comfortable option three.
• Patching Is Not The Villain This incident does not prove patching is dangerous. It proves blindly patching the entire production estate simultaneously is dangerous. Organisations that disabled Windows Update years ago because of one bad experience are practising avoidance, not patch management. Deployment rings, test machines, staged rollouts, and human oversight remain essential.
• Can We Talk About Testing? Remote Desktop Services is a widely used, business-critical feature. How did a security update that causes RDS to hang on configuration prompts make it through testing? Was the failure mode unseen, or was it deprioritised due to the urgency of fixing actively exploited vulnerabilities? Customers need transparency to make informed decisions.
• Would You Even Know? If RDS sessions started dropping or authentication slowed today, would monitoring systems alert administrators, or would users ring the helpdesk first? Crowdsourced diagnostics via user complaints is not monitoring. Proper alerting on authentication failures, session drops, and host responsiveness is necessary to detect issues before they escalate.
• So What Now? Do not panic or indiscriminately remove September updates. Check RDS environments for dropped sessions, sign-in failures, and hanging hosts. Microsoft’s current workaround is to stop, deallocate, and restart affected virtual machines. If systems are stable, continue monitoring. Confirmation of an issue does not mean universal breakage.
• Closing September 2026 encapsulates modern IT operations: nearly 1,000 security fixes, two actively exploited vulnerabilities requiring immediate patching, and a patch that may break Remote Desktop Services. The job is balancing security versus availability, urgency versus testing. Deployment rings are not optional. If all machines receive updates simultaneously, that is not a strategy. It is a countdown timer.

• https://www.bleepingcomputer.com/

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