This paper describes some of the challenges to understanding and ultimately automating drilling processes using models. Examples of models used to solve industry problems are torque and drag, stick slip, surge and swab, drillstring dynamics, and many more. Models may be data-driven, or physics based, steady state or dynamic, high fidelity or reduced order for execution speed and clarity. To learn from a high-fidelity model, data must be collected and fed to the model and parameters estimated to reproduce the behavior of interest.