Microsoft: September Windows updates break Always On VPN connections

On September 23 2026, Microsoft confirmed that the latest Windows 11 update released in September 2026 disrupts two core functions. The update stops File History from creating or maintaining backup copies of user files, and it also breaks the Always On VPN feature that keeps persistent corporate connections alive. The issue was first reported by multiple outlets on the same day, indicating a coordinated discovery of the regression. Coverage from CyberSecurityNews and Windows Latest both cite Microsoft’s official acknowledgement that the September update broke File History backups, describing the problem as a bug that caused the backup service to cease operation. Windows Latest noted that Windows 11 quietly stopped backing up files due to the new bug.

ZDNET followed with a step‑by‑step guide on how users can manually restore File History functionality, while PCWorld reported that Microsoft has issued a fix but that the patch will not install automatically. BleepingComputer focused on the VPN side, noting that the same September update interrupts Always On VPN connections used by many enterprises. File History is Windows 11’s native, continuous backup tool that copies changed files to an external drive or network location, providing users with a simple recovery option. Always On VPN, meanwhile, is a Microsoft‑endorsed solution that maintains a constant secure tunnel for remote workers, eliminating the need to reconnect manually. Because both features are integral to data protection and remote‑work reliability, a regression in a routine monthly update draws heightened attention from both consumer and enterprise audiences.

Enterprises depend on Always On VPN for secure remote access, so the connectivity break could affect business continuity. Going forward, readers should monitor Microsoft’s release cadence for an automatic rollout of the File History fix, as indicated by PCWorld’s note that the patch currently requires manual installation. Additional guidance may appear from the same outlets that have already published workarounds. Enterprises relying on Always On VPN are advised to watch for any further statements from Microsoft or updates from BleepingComputer that could address the connectivity problem.