Systems and methods for automating digital file classification are described. The systems and methods include generating a plurality of classifiers from a plurality of first features of a plurality of first digital files, each of the plurality of first digital files having one or more associated annotations. A plurality of second features extracted from a plurality of second digital files is sorted according to the plurality of classifiers. A distance vector is determined between the second features and respective first features for the corresponding ones of the classifiers and the determined distances are ranked. A subset of matched files is selected based on the ranking. The subset of matched files correspond to respective one or more associated annotations. One or more annotations associated with the subset of matched files are associated to subsequently received digital files using the corresponding ones of the classifiers.