Enigmatic and rarely collected, ambush bugs of the tribe Macrocephalini (Heteroptera: Reduviidae: Phymatinae) encompass a diverse group of predatory bugs armed with subchelate raptorial forelegs, a greatly enlarged scutellum, and elongate head. Macrocephalini is the most specious of the four tribes of ambush bugs, consisting of 20 genera and 154 species. They are represented in the Caribbean by several remarkable taxa that bear foretarsi, a trait unassociated with macrocephalines found elsewhere in the world. I here describe a new genus and species of Macrocephalini, Capricephala chiaroscuro gen. et sp. nov., native to the island of Hispaniola and one that bears striking differences to other phymatines known from that region.