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This paper reports on our ongoing practical experience designing, implementing, and deploying PTIME, a personalized agent for time management and meeting scheduling in an open, multi-agent environment. In developing PTIME as part of a larger assistive agent called CALO, we have faced numerous challenges, including usability, multi-agent coordination, scalable constraint reasoning, robust execution, and unobtrusive learning. Our research efforts provide basic solutions to the fundamental problems; however, integrating PTIME into a deployed system has raised other important issues for the successful adoption of new technology. As a personal assistant, PTIME must integrate easily into a user’s real environment, support her normal workflow, respect her authority and privacy, provide natural user interfaces, and handle the issues that arise with deploying such a system in an open environment.