Abstract Abstract—The most recent classification of the angiosperm order Gentianales (Thorne, 1992) includes four principal families: Apocynaceae, Gentianaceae, Loganiaceae, and Rubiaceae. Ever since Bentham (1857) the status of Loganiaceae has been questioned, and several segregates of that family have been proposed both before and after his treatment. In this study we present cladistic results that show Loganiaceae, sensu lato, to be a paraphyletic group definable only by plesiomorphies, with members showing closest relationships to other families of the order. As the impact of different character-state representations of polymorphic terminals remains largely untested, our morphological and phytochemical data were analysed both with restricted polymorphism coding as well as with the monomorphic "subtaxon" recoding method of Nixon and Davis (1991). Both approaches yield highly compatible results, and we here discuss a new classification of the Gentianales based on (i) monophyletic groups identified by outgroup analysis, and (ii) the maximal portrayal of evidence provided by subtaxon polymorphism recoding. Most prominently, the Loganiaceae sensu lato are divided into four segregate families, two previously named (Loganiaceae sensu stricto and Strychnaceae), and two defined as a result of this study (Gelsemiaceae, L. Struwe & V. A. Albert, stat. nov. and Geniostomaceae, L. Struwe & V. A. Albert, fam. nov.). Apocynaceae (incl. Asclepiadaceae), Gentianaceae (incl. Loganiaceae—Potalieae), and Rubiaceae remain as monophyletic families. Outgroup analysis supports both the monophyly of the Gentianales as well as the exclusion from the order of Buddleja, Desfontainia, Plocosperma, Polypremum, and Retzia (all Loganiaceae sensu Leeuwenberg and Leenhouts).