Several proposed or planned planetary science missions to Mars and other Solar System bodies over the next decade require subsurface access by drilling. This paper discusses the problems of remote robotic drilling, an automation and control architecture based loosely on observed human behaviors in drilling on Earth, and an overview of robotic drilling field test results using this architecture since 2005. Both rotary-drag and rotary-percussive drills are targeted. A hybrid diagnostic approach incorporates heuristics, model-based reasoning and vibration monitoring with neural nets. Ongoing work leads to flight-ready drilling software