A syringe rolling apparatus for initial rolling of a rolling diaphragm syringe from an unrolled state to a rolled state has a pressure jacket configured for receiving an empty, unrolled rolling diaphragm syringe, a piston reciprocally movable within the pressure jacket and configured for contacting an end wall of the syringe rolling diaphragm syringe to initiate a rolling of a flexible sidewall of the rolling diaphragm syringe, and a seal assembly configured for engaging an open discharge neck of the rolling diaphragm syringe. The seal assembly is in fluid communication with a source of pressurized fluid to pressurize an interior of the rolling diaphragm syringe during a distal movement of the piston. A method for initial rolling of a rolling diaphragm syringe from an unrolled state to a rolled state is also disclosed.