Scaling effects relating the maneuvering capabilities of a vehicle and the scale characteristics of a task environment play an important role in how the performance of a guidance system plays out. These effects are most significant for unmanned aerial vehicles because they are built in a much broader range of scales than manned vehicles. This paper investigates how scaling effects should be accounted for in the evaluation of guidance performance. It proposes a nondimensional quantity called the maneuvering environment scale ratio that captures the relationship between the maneuvering limits of a vehicle and the scale characteristics of a task environment. This paper also formalizes the idea of agent-environment dynamic fit for guidance tasks and uses the maneuvering environment scale ratio to measure the fit.Atask includes the vehicle dynamics, task environment, and mission objective. Agent-environment dynamic fit for a task is measured both quantitatively and qualitatively using the maneuvering environment scale ratio trajectory for an optimal solution. Finally, the paper demonstrates the application of the maneuvering environment scale ratio for quantifying the dynamic fit between an agent (guidance system) and environment using examples motivated by recent work in guidance systems benchmarking.