The native Hawaiian lobeliads include six genera and 141 described species, are the largest group of native plants endemic to the Hawaiian archipelago, and form one of the most striking examples of adaptive radiation and geographic speciation among plants on oceanic islands. The great majority of species are restricted to individual islands, each of known age; roughly one-fifth of all described species are thought to be extinct. Earlier analyses ­– based on seven plastid loci sequenced for 23 species across all six genera – indicated that this group was derived from a single colonist that arrived in the archipelago roughly 13 Mya, long before any of the current tall islands had emerged, and then radiated into a broad spectrum of growth forms, floral morphologies, and leaf shapes as the group dispersed southeastward toward younger islands, mostly from one island to the next younger in the chain in line with the so-called progression rule. To extend our analyses to a much larger share of the lobeliad radiation, supported by a much larger data set, we sequenced, assembled, and aligned the entire plastomes for nearly every extant Hawaiian taxon. We reconstructed lobeliad phylogeny using maximum likelihood applied to two data sets, involving exon-only sequences and full plastome assemblies. Only the exon-only phylogeny resolved a trichotomy of Brighamia-Delissea, Lobelia §Revolutella, and Trematolobelia-Lobelia §Galeatella. The last two clades are well supported as being sister to each other, forming a clade marked by terminal inflorescences and capsular fruits, in contrast to the axillary inflorescences and fleshy fruits seen in Brighamia-Delissea (fleshy only early in development in Brighamia) and Cyanea-Clermontia. Clermontia is strongly supported as being monophyletic, except for Cl. pyrularia embedded in Cyanea; the remainder of Clermontia is sister to the orange-fruited clade of Cyanea, with both jointly sister to the purple-fruited clade of Cyanea. This larger clade is itself sister to Apetahia/Sclerotheca from the Marquesas, Society Islands, and Cook Islands, pointing to an origin of this group of South Pacific lobeliads via long-distance dispersal from Hawaii. Analyses of historical biogeography point to several inter-island dispersal events within the Hawaiian archipelago, with almost all conforming to the progression rule within each genus and subgenus. We have also sequenced several hundred single-copy nuclear genes based on hybrid DNA capture; we will present analyses of these data soon to test for discordance and evidence for hybridization, introgression, and/or incomplete lineage sorting.