A technique is proposed for examining complex behaviors in the “pilot - vehicle - operational conditions” system using an autonomous situational model of flight. The goal is to identify potentially critical flight situations in the system behavior early in the design process. An exhaustive set of flight scenarios can be constructed and modeled on a computer by the designer in accordance with test certification requirements or other inputs. Distinguishing features of the technique include the autonomy of experimentation (the pilot and a flight simulator are not involved) and easy planning and quick modeling of complex multi-factor flight cases. An example of mapping airworthiness requirements into formal scenarios is presented. Simulation results for various flight situations and aircraft types are also demonstrated.