Provided is a crossbow cocking system comprising a sled, an elongated cocking cable, a first handle, and a second handle. The sled may have a first side having a first bowstring retainer, a first arm having a first set of handle engagement features adapted for engagement with a first handle, and a first pulley rotatably engaged with the first arm; and a second side having a second bowstring retainer, and a second arm having a second set of handle engagement features adapted for engagement with a second handle, a second pulley rotatably engaged with the second arm. The first and the second handle may each be engaged to the elongated cocking cable, and be ergonomically adapted to permit an associated user to operate the each handle during a cocking operation with a hand in a vertical hand position.