FreeBSD’s jail feature is one of the oldest and most mature OS-level isolation mechanisms in use today, powering hosting environments, container frameworks, and security sandboxes. But as with any large and evolving kernel feature, complexity breeds opportunity. This research asks a simple but critical question: If an attacker compromises root inside a FreeBSD jail, what does it take to break out?

To answer that, we conducted a large-scale audit of FreeBSD kernel code paths accessible from within a jail. We systematically examined privileged operations, capabilities, and interfaces that a jailed process can still reach, hunting for memory safety issues, race conditions, and logic flaws. The result: roughly 50 distinct issues uncovered across multiple kernel subsystems, ranging from buffer overflows and information leaks to unbounded allocations and reference counting errors—many of which could crash the system or provide vectors for privilege escalation beyond the jail.

We’ve developed proof-of-concept exploits and tools to demonstrate some of these vulnerabilities in action. We’ve responsibly disclosed our findings to the FreeBSD security team and are collaborating with them on fixes. Our goal isn’t to break FreeBSD, but to highlight the systemic difficulty of maintaining strict isolation in a large, mature codebase.

This talk will present our methodology, tooling, and selected demos of real jail escapes. We’ll close with observations about kernel isolation boundaries, lessons learned for other OS container systems, and a call to action for hardening FreeBSD’s jail subsystem against the next generation of threats.