Shipboard-landing maneuvers in rotorcraft piloting involve a number of unique challenges. Such maneuvers can be cognitively demanding even for experienced rotorcraft pilots. To minimize risk, these maneuvers are conducted within well-defined boundaries related to weather and visibility. In order to expand this envelope, technological aids are being proposed to augment decision making capabilities and reduce pilot workload without compromising safety. Our paper reports a cognitive task analysis, which involved interviews with four rotorcraft pilots, who were experienced in shipboard-landing maneuvers. Our results reveal points of high cognitive load, where expertise plays a critical role. We have articulated our understanding on why pilots are faced with difficulties during these critical points, which led us towards design recommendations and system requirements for technological aids. We have also identified a number of system limitations and quantities of interest, which may be useful in defining safety thresholds.