A mule shoe assembly for use in directional drilling which advantageously has releasable locking means to free the directional orienting tool from engagement with the outer mule shoe in situations where the drill bit may become stuck. The releasable locking means comprises a moveable pin which engages an aperture. A first configuration utilizes detent means and spring biasing of the pin. In a second configuration, the pin is adapted for locking engagement by pressurized downhole drilling mud, and may be disengaged from the aperture when pressure from drilling mud ceases. In a preferred embodiment the pin both has detent means and is spring biased, and also relies on drilling mud pressure to remain in locking engagement. The pin may be disengaged upon removal of drilling mud pressure and application of a positive separation force between the directional measurement tool and associated inner tool member, and outer mule shoe member.