A method and apparatus for automated engagement of a fitting coupled to a structure. A first member of a first engagement device is moved relative to a base in a first direction substantially parallel to an x-axis such that a tapered end portion of the first member passes through a hole in the fitting and moves towards a channel within a second member of a second engagement device. The tapered end portion of the first member is secured within the channel of the second member to thereby engage the fitting between the first engagement device and the second engagement device.