The Desktop History Tool presents users with a summary of the data they worked with throughout past days and weeks. The user’s own interaction history provides an invaluable self-organizing structure for the desktop interface. A user study was conducted to assess whether users could better discover and reconstruct important contexts by browsing and searching with desktop history, compared to the methods they typically used. We found that the history tool enabled users to discover a greater amount of important data and discover related data, allowing them to develop more thorough recreations of previous workspaces. We conclude that a time-based presentation of a user’s interaction history is a useful tool for supporting richer context-aware interfaces. Keywords Calendar, desktop, time-based computing, chronology, summarization, context, interaction history