Can You Trust an LLM with Your Life-Changing Decision? An Investigation into AI High-Stakes Responses

Large Language Models (LLMs) are increasingly consulted for high-stakes life advice, yet they lack standard safeguards against providing confident but misguided responses. This creates risks of sycophancy and over-confidence. This paper investigates these failure modes through three experiments: (1) a multiple-choice evaluation to measure model stability against user pressure; (2) a free-response analysis using a novel safety typology and an LLM Judge; and (3) a mechanistic interpretability experiment to steer model behavior by manipulating a "high-stakes" activation vector. Our results show that while some models exhibit sycophancy, others like o4-mini r emain robust. Top-performing models achieve high safety scores by frequently asking clarifying questions--a key feature of a safe, inquisitive approach--rather than issuing prescriptive advice . Furthermore, we demonstrate that a model's cautiousness can be directly controlled via activation steering, suggesting a new path for safety alignment. These findings underscore the need for nuanced, multi-faceted benchmarks to ensure LLMs can be trusted with life-changing decisions.