Critical Update Conflicts Cripple IIS Web Services
Microsoft has confirmed that recent Windows 11 updates are causing significant disruptions to IIS (Internet Information Services) websites, creating headaches for system administrators and web service operators. The problematic updates, KB5066835 and KB5065789 released during October 2025’s Patch Tuesday cycle, are generating widespread connection failures and authentication issues across affected systems. This development comes as Microsoft continues to address multiple Windows 11 update challenges affecting enterprise environments.
The company acknowledged that both Windows 11 version 24H2 and the upcoming 25H2 release are experiencing conflicts between the Windows updates and the HTTP stack driver (http.sys), resulting in failed localhost loopbacks and broken IIS-based authentication mechanisms. Affected users are reporting consistent “ERR_CONNECTION_RESET” error messages when attempting to access impacted web services.
Technical Breakdown of the IIS Disruption
According to Microsoft’s official statement, “Following installation of updates releases on or after September 29 (KB5066835 / KB5065789), server-side applications that rely on HTTP.sys may experience issues with incoming connections. As a result, IIS websites might fail to load, displaying a message such as ‘Connection reset – error (ERR_CONNECTION_RESET)’, or similar error.”
The scope of affected services includes websites hosted on http://localhost/ and various other IIS connections critical for internal operations and development workflows. Microsoft notes that the problem manifests under “a variety of conditions” including device internet connectivity, timing of update installation, and device restart schedules, meaning not all environments will experience the issue consistently.
Immediate Workaround Solution
While Microsoft develops a permanent fix, the company has provided IT administrators with a known issue rollback as an immediate workaround. The solution involves deploying a specific Group Policy that can be found in Computer Configuration > Administrative Templates section.
The available Group Policy download specifically addresses:
- Windows 11, version 24H2
- Windows 11, version 25H2
- Windows Server, version 2025
The required file, “Windows 11 24H2, Windows 11 25H2 and Windows Server 2025 KB5066835 251015_22001 Known Issue Rollback.msi,” provides temporary relief while Microsoft engineers work on a comprehensive resolution.
Broader Industry Implications
This IIS disruption comes at a time when Microsoft continues expanding AI capabilities across its Windows 11 ecosystem, creating additional complexity for system administrators managing enterprise deployments. The timing is particularly challenging for organizations balancing security updates with operational stability.
Meanwhile, other technology sectors continue advancing, with innovations appearing in agricultural technology solutions that increasingly rely on stable web services for data management and remote operations. Similarly, environmental technology developments including natural PFAS remediation techniques using wetland plants and fungi demonstrate how critical reliable computing infrastructure remains across diverse industries.
Economic and Operational Context
The Windows 11 update issues emerge alongside significant policy developments, including the upcoming UK Budget 2025 considerations that may impact technology investments and infrastructure planning. For industrial computing sectors, maintaining operational continuity remains paramount, particularly as organizations navigate financing challenges and supplier vetting requirements for critical infrastructure components.
Microsoft maintains its Windows Health dashboard with ongoing updates about this and other system issues, recommending that affected organizations implement the temporary Group Policy solution while awaiting a permanent patch. System administrators should monitor official channels for resolution timelines and additional troubleshooting guidance as it becomes available.
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