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Foundation models are increasingly deployed in socially sensitive domains such as education, mental health, and caregiving, where failures are often cumulative and context-dependent. Existing guardrail approaches -- ranging from training-time alignment to prompting, decoding constraints, and post-hoc moderation -- primarily provide empirical risk reduction rather than enforceable behavioral guarantees, and largely treat safety as a property of individual outputs rather than interaction trajectories. We reframe guardrails as a problem of runtime behavioral control over interaction trajectories, drawing on robotics to introduce formal constructs for constraint enforcement in uncertain, closed-loop systems. We instantiate these ideas in the Grounded Observer framework and apply it across three real-world deployments: small talk, in-home autism therapy, and behavioral de-escalation in schools. Across settings, the framework enables runtime interventions that mitigate drift into undesirable interaction regimes while adapting to diverse social contexts. We discuss extensions to the framework and propose research directions toward stronger guarantees.