This chapter describes a multi-agent thinking swarms operating collaboratively with a human team on the ground. It is the result of a multi-year project funded by the Australian Defence Force, led by Mission Systems, to determine the “art of the possible” in regard to what can be achieved with today’s technology, as applied to human-machine teaming at the tactical level. We show that robots and humans need to guide one another to achieve compelling results and that although none of this is easy, there are techniques that allow us to build a scalable system of systems to meet real-world goals.