We explore an executive function that performs adaptive, introspective reasoning for autonomous systems in challenging situations. This chapter presents a definition of the problem using cartoon examples for electronic warfare and submarine surveillance. A case study of neural processes in therapy for Post-traumatic Stress Disorder (PTSD) is discussed; PTSD provides both a second modelling challenge and an architectural inspiration for executive reasoning. The main body of the chapter is towards a technique for working with virtual and physical agent models in mixed human/machine systems. The architecture supposes a second-sorted reasoning system with complementary reasoning power over situations, influences and unknowns.