The mammalian premaxilla, which bears the incisor teeth, is composed of a body and two processes (nasal and palatine) that articulate with other rostral bones via four cranial sutures. In bats, the premaxilla is modified in many ways, and this variation has been extensively used in bat systematics. The premaxilla has provided characters to diagnose a number of important taxonomic groupings—most notably, the division of Microchiroptera into the infraorders Yinochiroptera and Yangochiroptera. Recent molecular studies have challenged the monophyly of Microchiroptera, and several families have been transferred to clades other than those in which they were placed traditionally. Because premaxillary characters have figured prominently among those used to establish the traditional classification of bats, we compared the anatomy of the bone across suprageneric bat groups and provide revised descriptions of its variation. On the basis of extensive material examined, we generated 16 new characters, of which at least 12 are partially applicable to all Chiroptera, and several of which are informative within specific bat groups. Three new characters code variation in the basic structure of the chiropteran premaxilla in a new way. As a result, the traditional character defining Yinochiroptera (a “movable premaxilla”) was found to lack an anatomical basis; by contrast, Yangochiroptera was still supported. Still, a tree search using just the new premaxillary characters recovered Yinochiroptera as monophyletic. Even with a low character-to-taxon ratio, premaxillary characters recover a number of clades recognized in recent phylogenetic studies of bats. Mapping of characters onto the latest molecular and morphological chiropteran trees required many more extra steps in the former than in the latter. Our interpretation of premaxillary variation in bats suggests two opposing trends in different lineages: one toward weakening and eventual loss of the bone, and the other toward a strengthening via suture fusion. We conclude that, despite some homoplasy, the chiropteran premaxilla is richer in potentially phylogenetically informative characters than previously thought and that it should be explored further in systematic studies of bats at a variety of systematic levels.