A dynamic differential diagnosis training and evaluation system incorporates a beginner student learning mode, a beginner student test mode, an advanced student learning mode, and an advanced student test mode for training, nurturing, and evaluating dynamic differential diagnosis (dynamic DDx) reasoning skills for patient condition determination. In a preferred embodiment of the invention, the dynamic differential diagnosis training and evaluation system incorporates one or more computerized user interfaces for displaying, choosing, and interacting with a simulated virtual patient, hypotheses selections for the patient condition determination, simulated physical exam selections, simulated medical test selections, simulated medical test results, a computerized expert's feedback and answers, and an iterative differential diagnosis (DDx) list modification and refinement process that simulates real-life dynamic differential diagnosis (dynamic DDx). Furthermore, the dynamic differential diagnosis training and evaluation system can also incorporate healthcare education contents generated from a healthcare content authoring platform.