Adiantopsis Fée (Pteridaceae) is a relatively unstudied tropical cheilanthoid fern genus. In the present work, we evaluated the taxonomy and relationships among Caribbean Adiantopsis by examining 136 characters from approximately 500 herbarium specimens. This study identified nine Caribbean Adiantopsis species, three of which are newly described (A. parvisegmenta, A. pentagona, and A. vincentii). Additionally, an intriguing pattern of morphological and reticulate evolution was revealed by the analyses. Adiantopsis consists of three different laminar morphologies; palmate, pedate, and pinnate. The two pedate taxa are hypothesized to be fertile allotetraploid derivatives of the palmate A. radiata (L.) Fée and two different pinnate taxa. In this regard they parallel the origin of the South American A. ×australopedata Hickey, M. S. Barker & Ponce. Based on our analyses, it appears that pedate laminar morphologies in Adiantopsis independently originated multiple times via hybridization. This study provides testable hypotheses of morphological and reticulate evolution in the genus and presents a novel view of Caribbean Adiantopsis.