Reentrant structures have been deemed necessary for repelling low‐surface‐tension liquids. In this article, a novel manufacturing methodology using the roll‐to‐roll process to enable continuous manufacturing of reentrant structures over large areas on a polymeric film was demonstrated. A two‐stage process, composed of embossing followed by post‐compression, allowed the fabrication of reentrant structures, which cannot be easily fabricated using other processes over large areas in a continuous manner. The treatment of the reentrant surface structures with an additional coating of 1H,1H,2H,2H‐perfluorooctyltrichlorosilane layer provided liquid repellency with contact angles of 155 and 140°, respectively, for water (Ylv = 72 mN m−1) and diiodomethane (Ylv = 50 mN m−1). © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 46980.