Embodiments described herein relate to extendable sleepers for a tractor and methods of operating such a sleeper. In one embodiment, the tractor is connectable with a trailer. The trailer has a front surface. The extendable sleeper comprises a fixed portion disposed on the tractor, an extendable portion attached to the fixed portion, the extendable portion being movable between a retracted position and an extended position, and a mover operatively connected with the extendable portion for moving the extendable portion between a retracted position and an extended position. A control system is operatively connected with the mover for controlling operation of the mover. The control system operates in an extension mode where position of the extendable member is adjustable, a teach mode where a significant location of the extendable member is programmed into the control system, and an automatic mode where position of the extendable member is maintained.