Described is a system and method including a user interface to manage sets of digital data (e.g., files) such as digital photographs or email messages. The system and method comprise a rapid sort mechanism and an underlying support mechanism that associates metadata with each set of digital data, including annotation metadata obtained from the sort mechanism. As the user scrolls through images that represent the sets of digital data and categorizes them, metadata as to its particular categorization or lack of categorization is implicitly obtained and associated with each set of digital data. Grouping of sets of digital data into clusters is also provided, with a visual indication as to which cluster a set of digital data belongs. With respect to digital photography, the system and method makes annotating and classifying digital photographs significantly easier and faster than contemporary photograph management mechanisms.