Real-world large language model (LLM) agents must master strategic tool use and user preference optimization through multi-turn interactions to assist users with complex planning tasks. We introduce COMPASS (Constrained Optimization through Multi-turn Planning and Strategic Solutions), a benchmark that evaluates agents on realistic travel-planning scenarios. We cast travel planning as a constrained preference optimization problem, where agents must satisfy hard constraints while simultaneously optimizing soft user preferences. To support this, we build a realistic travel database covering transportation, accommodation, and ticketing for 20 U.S. National Parks, along with a comprehensive tool ecosystem that mirrors commercial booking platforms. Evaluating state-of-the-art models, we uncover two critical gaps: (i) an acceptable-optimal gap, where agents reliably meet constraints but fail to optimize preferences, and (ii) a plan-coordination gap, where performance collapses on multi-service (flight and hotel) coordination tasks, especially for open-source models. By grounding reasoning and planning in a practical, user-facing domain, COMPASS provides a benchmark that directly measures an agent's ability to optimize user preferences in realistic tasks, bridging theoretical advances with real-world impact.

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