Cyclohexane is a textbook model used to discuss the concepts of molecular strain and conformational interconversion in undergraduate organic chemistry courses. The rate of interconversion and/or relative population of conformers can be impacted by temperature, solvent environment, and chemical substitutions on the cyclohexane ring. In this work, we investigate the ability of classical models to capture this behavior. Additionally, we use quantum chemical calculations to help parameterize components of the classical force field and quantify the roles of these components on determining the rates and relative populations. These insights deepen our understanding of cyclohexane's behavior in diverse chemical environments, offering new information about a textbook example.