Real time measurements and development of sensor technology are research issues associated with robustness and safety during oil well drilling operations, making feasible the diagnosis of problems and the development of a regulatory strategy. The major objective of this paper is to use an experimental plant and also field data, collected from a basin operation, offshore Brazil, for implementing smart monitoring and decision making, in order to assure drilling inside operational window, despite the commonly observed disturbances that produce fluctuations in the well annulus bottom hole pressure. Using real time measurements, the performance of a continuous automated drilling unit is analyzed under a scenario of varying levels of rate of penetration; aiming pressure set point tracking (inside the operational drilling window) and also rejecting kick, a phenomenon that occurs when the annulus bottom hole pressure is inferior to the porous pressure, producing the migration of reservoir fluids into the annulus region. Finally, an empirical model was built, using real experimental data from offshore Brazil basins, enabling diagnosing and regulating a real drilling site by employing classic and advanced control strategies.