Every year, professional classifiers at West Group manually classify over 350,000 headnotes, or abstracts of judicial opinions, across approximately 82,000 separate classes of the Key Number System. Although most headnotes are classified from the memory of the classifiers, a significant number are difficult and thus costly to classify manually. Accordingly, the inventors devised systems, methods, and software that facilitate manual classification of headnotes and documents generally and hard-to-classify headnotes particularly. One exemplary system provides a graphical user interface that concurrently displays an unclassified headnote, a ranked list of one or more candidate classes, a candidate class in combination with adjacent classes of the classification system, and at least one classified headnote that is associated with one of the candidate classes.