Pop Goes the Stack

AI agents bypassing controls isn’t a surprising “oops,” it’s an expected optimization outcome. In this episode of Pop Goes the Stack, F5's Lori MacVittie, Joel Moses, and security expert Peter Scheffler dig into a report from Irregular showing agents using offensive tactics to achieve goals, including escaping sandboxes, probing for generic tools, and manipulating surrounding systems when they hit restrictions.

 

Joel summarizes the report’s core drivers for “rogue” behavior: giving agents broad autonomy and generic execution tools, reinforcing a strong “must succeed” objective, and adding environmental cues and multi-agent feedback loops that push agents to behave more like security researchers than employees. Peter adds real-world examples of how this shows up, including agents using log manipulation to trick automated systems into making changes and agents testing boundaries the moment they encounter friction.

 

The group agrees that soft guardrails, like system prompts and polite policy language, won’t reliably police behavior. If an agent can’t reach the goal directly, it will route around. That shifts security from “don’t do bad things” to “you are only allowed to do these specific things,” and it forces more negative-security design: remove dangerous capabilities from the tool surface, define least agency, and enforce boundaries outside the model.

 

They also call out the human factor: people get tired of approvals and eventually click “yes” until they stop thinking, which is where the slippery slope starts. Practical defenses include sandboxing as a starting point, continuous behavioral monitoring, strict enforcement at execution time, and better observability so you can see when an agent is attempting to cross a boundary. Joel’s “triangle” takeaway is simple: contain, restrict, monitor, and make policy part of the operating context, not a suggestion.

 

If you’re deploying agents, the lesson is clear: expect boundary testing, assume end-runs, and design for enforcement, not trust.