Evolving our calendar assistant Reclaim to be AI-native without starting over

Calendars hold more than just blocks of time. They reflect how people plan their days, coordinate with others, and make room for what matters to them. Reclaim, the Dropbox-owned calendar assistant, helps manage that complexity by using AI to find and adjust time for tasks, habits, and meetings. That approach works well when inputs and expected outcomes are clear. But people also use Reclaim for scheduling that’s less straightforward.

As AI assistants and natural-language interfaces became more capable, they opened up a new way for people to use Reclaim. We imagined situations where users could describe a scheduling goal in their own words, even when it didn’t map neatly to an existing setting or command. Words alone wouldn’t be enough to determine what should happen on a real calendar, though. Reclaim still needs the context that gives requests meaning, including what’s already scheduled, when a user is available, and which preferences and commitments impact changes.

Connecting natural-language requests with the surrounding calendar context could help people spend less time figuring out which settings or actions to use. But building the experience required more than adding an AI interface to the existing product. We needed to rethink how Reclaim turned conversational requests into calendar changes while preserving the scheduling system already in place.

Evolving Reclaim for AI without starting over