Simulation techniques are increasingly becoming popular in recent years as a way of simulating oil drilling processes. Among them, directional drilling is a specific method that benefits enormously from such numerical techniques, inasmuch as the estimation of the wellbore curvature is crucial and cannot be properly estimated through approximate geometry methods. We present here some of the latest advances in bit contact dynamics, wellbore update algorithms, and experimental validation of side cutting, in the context of a finite element (FE) and finite segment simulation framework. The framework is based on the high-fidelity dynamic simulation of the mechanical system, including detailed geometry, large displacements, and accurate contact forces. The theoretical aspects, along with the experimental results, are thoroughly presented. Overall, this paper constitutes a step toward a more deterministic way of calculating build rates and designing downhole drilling tools.