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Calendar scheduling makes the trust problem concrete: an assistant must coordinate with other assistants while deciding what to reveal about the person it represents. We introduce CalBench, a controlled benchmark for multi-agent calendar scheduling under private information. In each task, $N$ agents manage separate private calendars and schedule a stream of $M$ incoming meetings while minimizing disruption costs. Because no agent can inspect another agent's calendar, success requires language-mediated coordination rather than centralized planning. CalBench generates solvable scenarios with CP-SAT oracle solutions and decentralized non-LLM reference protocols, enabling evaluation of task success, excess cost, communication efficiency, burden fairness, and privacy leakage under matched information constraints. 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