Crowdsourcing is an overarching term that denotes a number of ways to use the web as means to enlist a large number of individuals to perform a particular task. The tasks can range from simply providing an opinion, to contributing material, to solving a problem. Because the term crowdsourcing is used to denote a variety of activities in many different contexts, strong opinions have formed in many minds. This paper is an attempt to inform the reader of the complexity that underlies the simple term “crowdsourcing.” We then describe the connection between the DARPA Adaptive Vehicle Make program with the potential limitations of crowdsourcing complex tasks using examples from industry. Using these examples, we present a research motivation detailing areas to be improved within current crowdsourcing frameworks. Finally, an agent-based simulation using machine learning techniques is defined, preliminary results are presented, and future research directions are described.