Thermodynamic design and analyses have been carried out on a multiple extraction regenerative Rankine cycle employing a recent software called CyclePad. A synergistic combination of qualitative physics and artificial intelligence techniques have been used to develop Cycle-Pad to assist in teaching, design and research in applied thermodynamics and advanced energy conversion systems. It provides an articulate virtual laboratory, in terms of visualisation of the schematic combination of a variety of thermodynamic cycles. A thorough sensitivity analysis has been carried out to help optimise the regenerative Rankine cycle in terms of thermal efficiency as a function of the extraction pressures and the splitting fractions. Numerical results and trend plots are provided. Such studies demonstrate that analyses of complex cycles can now be carried out, as part of classroom instruction as well, employing such a tool.