This case study investigated the experience of a military helicopter pilot trainee during formation flight. Formation flight is a technique used in military operations, consisting of maneuvering safely around a Lead helicopter by controlling the rate and direction of motion to avoid collisions. Using the Course-of-Action framework, we described the pilot's cognitive activity during formation-flight maneuvers (join-up patterns) in a practice session from his own perspective to provide insights into his lived experience. Focus was placed on the situational elements that were meaningful to the pilot at a given moment (i.e., Representamen), and how these meaningful situational elements were guided by his situated concerns (i.e., Involvement). Data were collected in two steps: (1) collection of activity traces during formation flight training and (2) self-confrontation interviews using these activity traces in which the pilot was invited to relive his experience and describe his activity. The results indicated five typical representamen and four typical involvements, and revealed eight different associations between these typical representamen and typical involvements over the course of the maneuvers. The discussion addresses how the description of these associations provides a better understanding of the pilot's activity during formation maneuvers and proposes possible extensions of this study.