The paper describes a study conducted by the University of Windsor Vehicle Dynamics and Control Research Group into the stability of coupled vehicles, e.g., truck-trailer combinations. Several instabilities associated with truck-trailer combinations have been well documented, and have been predicted using mathematical models. Despite having relatively low complexity the classic truck-trailer model, a simple two body, three degree of freedom, linear model has been used extensively in coupled vehicle stability analyses. The aim of the presented work was to extend the conventional coupled vehicle analysis with a set of more elaborate mathematical models evaluating various vehicle configurations. Using in-house multibody dynamics software the linearized equations of motion of three dimensional models were automatically generated for various coupled vehicle configurations with general and military applications. Stability analyses were conducted over a range of expected operating speeds. The paper concludes by discussing the efficacy of the proposed models and presenting design and operational recommendations to improve the stability of coupled vehicles.