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While single-turn safety mechanisms are relatively mature, extended interactions reveal structural vulnerabilities where initial alignment degrades over time. This paper empirically characterizes two observed failure modes across multiple state-of-the-art LLMs: Safety Drift, the gradual erosion of declared safety intent leading to constraint-violating actions (e.g., textual refusal followed by reconnaissance and unsafe execution), and Operational Hallucination, persistent repetitive tool calls indicative of flawed state perception (e.g., livelocks even in legitimate tasks). 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