The characteristics of pattern replication and releasing in a roll-to-roll ultraviolet- (UV) curing embossing process were investigated. The roll embossing system was designed for large-area continuous embossing, with employment of a fast curing resin, a heat damage protector, and a surface energy reducing coating. A 60° V-groove pattern with a groove period of 30 µm was embossed. It was found that the replication quality was profoundly influenced by the pattern geometry, the pattern direction, and the mold surface energy. In particular, the pattern direction significantly affected the edge sharpness and the surface topography of replicated features. In the parallel groove mode, a significant amount of tearing and sliding occurred, whereas in the transverse groove mode, biting marks were observed on the side wall of the V-groove. A simple mechanical model was used to explain the difference in pattern releasing with different pattern layouts. The replication quality was found to be significantly improved with the application of a fluorinated coating on the roll mold.