In a world of electronic calendars, the prospect of intelligent, personalized time management assistance seems a plausible and desirable application of AI. PTIME ( Personalized Time Management ) is a learning cognitive assistant agent that helps users handle email meeting requests, reserve venues, and schedule events. PTIME is designed to unobtrusively learn scheduling preferences, adapting to its user over time. The agent allows its user to flexibly express requirements for new meetings, as they would to an assistant. It interfaces with commercial enterprise calendaring platforms, and it operates seamlessly with users who do not have PTIME. This article overviews the system design and describes the models and technical advances required to satisfy the competing needs of preference modeling and elicitation, constraint reasoning, and machine learning. We further report on a multifaceted evaluation of the perceived usefulness of the system.