Embodiments can provide dynamic assessment by an expert system software (ESS) module. The ESS module may determine a minimum set of diagnostic questions to identify a student's strengths and/or weaknesses for a given subject matter. Each diagnostic question may be a unique question variant generated from a dynamic question template. The ESS module may automatically and dynamically build a personal lesson plan that includes lessons on topics of the subject matter that the student has not mastered. The ESS module may dynamically modify the personal lesson plan to change a lesson and/or add lesson(s) considered by the ESS module as necessary for the student to master the subject matter. Given the ESS module's knowledge on various components of a question such as equation(s) used to produce a correct answer to the question, the ESS module may generate image(s), customized hint(s), customized explanation(s), and/or examine student solutions in step-by-step fashion.