A rotary cutting tool with enhanced bump-off capability is disclosed. The cutting tool includes a tool shank having a pocket. A replaceable cutting head is at least partially disposed within the pocket of the tool shank with an interference fit. A coupling pin assembly is at least partially received within a bore of the tool shank. The coupling pin assembly comprises a sleeve member and a coupling pin at least partially disposed within the sleeve member. The sleeve member includes an upper portion and a lower portion having a non-circular cross-sectional shape with a bump-off surface. An actuation screw contacts the coupling pin assembly and causes the replaceable cutting head to move relative to the tool shank. The bump-off surface of the lower portion of the sleeve member extends radially outward with respect to the coupling pin by a distance, D, thereby providing enhanced bump-off capability.