A pen needle assembly apparatus includes a tray (34), a movable clamping assembly (36) for gripping a pen needle assembly (18), and an actuator assembly (38). The tray (34) has a top end (42), a bottom end (40), and an inner cavity for storing used pen needle assemblies. The clamping assembly (36) in one embodiment includes at least one movable clamping member (48) that is movable between a first position where the clamping member engage and grip the outer cover (22) of the pen needle assembly (18) so that the needle hub (16) can be separated from the outer cover (22) and placed back in the outer cover (22) after use of the pen needle. The actuator assembly (38) is connected to the movable clamping member (48) where movement of the actuator releases the movable clamping member to move to the open positon and release the outer cover of the pen needle assembly. The base (32) of the apparatus can include an opening for engaging the inner shield (24) of the pen needle assembly to assist in removing the inner shield (24) from the needle hub (16).