The association between insect herbivores and vascular plants represents one of the greatest success stories in terrestrial evolution. Specific mechanisms generating diversity in the association remain poorly understood, but it has become increasingly clear that microbes play important roles in mediating plant–insect interactions. Previous research on phytoplasmas (Acholeplasmatales: Acholeplasmataceae), a diverse group of plant-pathogenic bacteria, and their hemipteran insect vectors suggests that this system provides a new model for understanding how interactions among distantly related but ecologically associated groups of organisms can drive evolutionary diversification. Phytoplasma infections affect the phenotypes of both plants and vectors, altering functional traits (e.g., diet breadth) and mediating host shifts which may, in turn, alter genetic and phylogenetic patterns. This review highlights previous research on the functional ecology and phylogenetic components of phytoplasma-plant-vector (PPV) associations relevant to the evolutionary diversification of this system. Although phytoplasmas and their hosts occur in most terrestrial biomes and have evolved together over the past 300+ million years, major gaps in knowledge of PPV associations remain because most prior research on the system focused on strategies for mitigating effects of phytoplasma diseases in agroecosystems. Study of this system within a broader evolutionary context could help elucidate mechanisms by which interactions between insect herbivores, microbes, and plants drive biological diversification and also help predict the emergence of diseases affecting agriculture. Future research should more thoroughly document PPV associations in natural habitats, examine the relative prevalence of cospeciation versus host shifts in this system, and test possible macroevolutionary consequences of host manipulation by phytoplasmas.