Besides observing the pilot passively and providing contextual assistance in light of carrying out various flight tasks more efficiently, engaging the pilot in a dialogue creates an opportunity to go beyond passive monitoring of pilot’s activities and flight status, by actively requesting for input information from the pilot, enriching therefore the knowledge of the pilot assistance system on the context. Such a dialogue has to be dynamic, concise and goal-directed, as it can be safety critical. In this paper, we demonstrate how FOND-planning-based dialogue agents can be applied to the use case, while also leveraging recent advances in natural language understanding and text-to-speech synthesis, in order to generate instances for the computation of plans as guidance to the pilot in an automated manner problem.