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Structurally diverse queen pheromones and fertility signals regulate the reproductive division of labor of social insects, such as ants, termites, some bees, and some wasps. The independent evolution of sociality in these taxa allows for the exploration of how natural history differences in sender and receiver properties led to the evolution of these complex communication systems. While describing the different effects and the structural diversity of queen pheromones, we identify two major syndromes that mostly separate ants and wasps from bees and termites in their use of different pheromone classes. We compare olfactory receptor evolution among these groups and review physiological and hormonal links to fecundity and pheromone production. We explore the cases in which queen pheromone evolution is conserved, convergent, or parallel and those in which queen pheromone responses are more likely to be learned or innate. More mechanistic information about the pathways linking fecundity to queen pheromone production and perception could help close major knowledge gaps.