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The question of what it means and what it takes for an autonomous system to consider another autonomous system justifiably trustworthy must be addressed by all who seek to integrate intelligent machine agents into real-world operations. A satisfactory answer to this question is an essential component in accepting autonomous machine decision-making in safety-critical and time-critical environments, such as aviation. Historically, simulation platforms for test and evaluation of complex systems have proven to be effective in assessing performance and contributing to decisions on the fitness of systems to operate in current general and commercial aviation airspace. Moreover, simulations have informed the definition of safety-critical constraints. However, as machine systems progressively take on responsibilities for decision-making traditionally supplied by humans, simulations require enhancement. Mixed reality simulation that integrates real-world platforms and data or high-fidelity simulation data in a sim-to-flight paradigm provides insight into agent interaction and the rationale behind autonomous agent decision-making as well as the capacity for seamless integrated implementation, testing, and operation of systems. Strong simulation capabilities are especially important in the presence of algorithms that hold great promise in decision-making yet increase the uncertainty in the system. Autonomy Teaming and TRAjectories for Complex Trusted Operational Reliability (ATTRACTOR) is a subproject of NASA’s Convergent Aeronautics Solutions (CAS) Project. ATTRACTOR’s objective is to build a basis for understanding trust and trustworthiness in multi-agent autonomous teams, and thus to inform future certification of safety-critical and time-critical autonomous systems in aviation. Because the concepts of trust and trustworthiness must be addressed in a context, ATTRACTOR has chosen Search and Rescue (SAR) in dynamic and unstructured environments, with emphasis on search, as its design reference mission (DRM). During dynamic planning and execution of trajectory-based operations, autonomous agents determine their trajectories given an assigned mission or missions and call for assistance from an appropriate teammate when needed. This experience along with the attendant human-machine and machine-machine interactions, serve as a platform for developing approaches to identifying and measuring trustworthiness and increasing trust. In this paper, we give an overview of some of ATTRACTOR’s research and development activities, findings, and ongoing work.