An example system includes an aerial vehicle, a sensor, and a winch system. The winch system includes a tether disposed on a spool, a motor operable to apply a torque to the tether, and a payload coupling apparatus coupled to the tether and configured to mechanically couple to a payload. The system also includes a repositioning apparatus configured to reposition the payload coupling apparatus in at least a horizontal direction. A control system is configured to control the aerial vehicle to deploy the payload coupling apparatus by unwinding the tether from the spool; receive, while the aerial vehicle hovers above the payload and from the sensor, data indicative of a position of the payload coupling apparatus in relation to the payload; and reposition, using the repositioning apparatus and based on the data, the payload coupling apparatus in the horizontal direction to mechanically couple to the payload.