AI agents trap themselves in obsolete rules, degrading in production

Gregory Green's production stack research shows that deployed AI agents fail to adapt when their operating constraints become outdated—a liability as organizations scale agentic systems into workflows where rule changes happen constantly. The "32% problem" Nicole Dove identifies (teams over-trusting AI outputs despite known brittleness) exposes a deeper gap: guardrails that prevent hallucinations also prevent agents from recognizing when those guardrails themselves need updating. Teams face a choice between safety and autonomy rather than building systems that can safely evolve their own constraints.