Systems and methods of the present invention provide for storing textbook data, a glossary, and problems within a database; identifying a problem's guided solution, and a keyword within the solution matching an entry within the glossary, from which a skill tag is associated. The disclosed system then automatically generates an assessment including an assessment problem associated with the skill. If an incorrect response is received for the assessment problem, the database is updated to associate a user that input the response with the assessment problem and a skill. The system then automatically generates a customized exercise assignment associated in the database with the skill.
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