Heteroptera, or true bugs, are part of the most successful radiation of nonholometabolous insects. Twenty-five years after the first review on the influence of cladistics on systematic research in Heteroptera, we summarize progress, problems, and future directions in the field. The few hypotheses on infraordinal relationships conflict on crucial points. Understanding relationships within Gerromorpha, Nepomorpha, Leptopodomorpha, Cimicomorpha, and Pentatomomorpha is improving, but progress within Enicocephalomorpha and Dipsocoromorpha is lagging behind. Nonetheless, the classifications of several superfamily-level taxa within the Pentatomomorpha, such as Aradoidea, Coreoidea, and Pyrrhocoroidea, are still unaffected by cladistic studies. Progress in comparative morphology is slow and drastically impedes our understanding of the evolution of major clades. Molecular systematics has dramatically contributed to accelerating the generation and testing of hypotheses. Given the fascinating natural history of true bugs and their status as model organisms for evolutionary studies, integration of cladistic analyses in a broader biogeographic and evolutionary context deserves increased attention.