U.S. Naval aviation, similar to units in its sister services, uses the family of simulators approach to training that enables trainees to build on skills progressively throughout the training pipeline. The progression begins with system skills (e.g., buttonology), continues to individual tasks (e.g., understanding radar data), and concludes with aircrew coordination for tactical proficiency (e.g., prosecuting an anti-submarine warfare mission). However, this approach requires workarounds (e.g., instructor role-players) or a tradeoff in fidelity when trainees reach a point in skills training that requires communication from other crewmembers while still conducting standalone training tasks. With recent technological advances in speech recognition (Stensrud, Newton, Atkinson & Killilea, 2015), the feasibility of incorporating synthetic role-playing crewmembers into a dynamic training event has increased. This paper highlights the need for this technology within the target transition community, the P-8A Poseidon, as part of its part-task training simulator. Successful integration will promote efficient use of resources (e.g., manpower), increased fidelity through the availability of realistic crew communication and coordination, and flexibility in crew composition availability. The prototype architecture is discussed, including the integration of speech capabilities (e.g., recognition, dialog, understanding, synthesis) and behavior modeling to yield an interactive model for P-8A crewmember agents. Next, the authors provide lessons learned and challenges to the technological implementation, as well as the sustainment, given the rapid pace of tactic and protocol changes that will impact the underlying technologies. Additionally, the authors provide results of a preliminary usability analysis of the system, including primary stakeholder fleet evaluations regarding system reliability and synthetic voice analysis. Finally, the authors highlight the importance of performance testing, offer suggestions for adapting the technology to other use cases, and discuss future directions for interactive system research and development.