Abstract: Various embodiments of a nail gun assembly and a method of using same are disclosed. The nail gun assembly includes a nail gun including a housing and a nailing mechanism disposed at least partially within the housing. The assembly also includes a guide connected to the housing that includes a contact surface that forms a guide plane that is substantially orthogonal to a tool axis of the nail gun, where the contact surface is adapted to contact a working surface of a workpiece. The nailing mechanism is adapted to be manipulated from a deactivated state to an activated state when the contact surface of the guide is in contact with the working surface and an angle ? formed between the tool axis and a normal to the working surface is no greater than a predetermined angle.