Doryopteris J. Sm. includes roughly 20 species of pantropical cheilanthoid ferns. Four species of Doryopteris are endemic to the Hawaiian Islands, including two widespread species found across all major islands and two narrow endemics known from small, isolated populations. The two widespread endemics are thought to hybridize, producing Doryopteris x subdecipiens. The evolutionary origins of these Hawaiian species, and their relationships to each other, are still unknown.  Using a dataset of 316 nuclear loci generated by target enrichment from a sample of 69 individuals of Doryopteris and outgroups, we investigate the evolutionary relationships between the four endemic Hawaiian species of Doryopteris and the status of the putative hybrid. We find that while most Hawaiian Doryopteris samples fall together in a single clade (suggesting a single colonization of Hawai’i), one individual of Hawaiian D. cf. decipiens falls instead with a clade of the broadly-distributed species, Doryopteris concolor. This pattern suggests that while one dispersal event and subsequent radiation led to the current distribution of most Doryopteris across the Hawaiian islands, a second migration event contributed to previously undescribed diversity in Hawaiian Doryopteris. Furthermore, all Hawaiian species appear nested within the widely-distributed D. concolor complex, which occurs across the Americas, Pacific islands, and tropical Africa. However, our molecular data fail to recover the individual Hawaiian species as reciprocally monophyletic clades. Complex population dynamics, such as ongoing/ incipient speciation, hybridization, or extensive gene flow, may be contributing to the lack of monophyly within most Hawaiian species, and further population genetic analyses may be needed to untangle relationships within the Hawaiian clade.