Continuing the exploration of transformative legal risk management, this chapter addresses the remaining two risk dimensions that govern a VUCA environment: complexity and ambiguity. Complexity is an environment that contains numerous interconnected parts, accepts inputs, generates outputs, and develops a capacity to learn and remember. The fourth and final dimension of VUCA is ambiguity. Especially challenging for firms deploying legal knowledge, ambiguity is an environment where causes and effects propelling events forward are largely unknown, the firm does not know whether an organized system will emerge, and little historical precedent exists for determining the most appropriate course of action. The chapter defines complexity and ambiguity, explains how they are applicable to legal risk, and articulates strategies for firms to use their legal knowledge to anticipate and address complex and ambiguous legal problems.