This thesis introduces COMPLEXITY TUTOR, a tutoring system to assist in learning abstract proof-based topics, which has been specifically targeted towards the population of computer science students studying theoretical computer science. Existing literature has shown tremendous educational benefits produced by active learning techniques, student-centered pedagogy, gamification and intelligent tutoring systems. However, previously, there had been almost no research on adapting these ideas to the domain of theoretical computer science. As a population, computer science students receive immediate feedback from compilers and debuggers, but receive no similar level of guidance for theoretical coursework. One hypothesis of this thesis is that immediate feedback while working on theoretical problems would be particularly well-received by students, and this hypothesis has been supported by the feedback of students who used the system. This thesis makes several contributions to the field. It provides assistance for teaching proof construction in theoretical computer science. A second contribution is a framework that can be readily adapted to many other domains with abstract mathematical content. Exercises can be constructed in natural language and instructors with limited programming knowledge can quickly develop new subject material for COMPLEXITY TUTOR. A third contribution is a platform for writing algorithms in Python code that has been integrated into this framework, for constructive proofs in computer science. A fourth contribution is development of an interactive environment that uses a novel graphical puzzle-like platform and gamification ideas to teach proof concepts. The learning curve for students is reduced, in comparison to other systems that use a formal language or complex interface. A multi-semester evaluation of 101 computer science students using COMPLEXITY TUTOR was conducted. An additional 98 students participated in the study as part of control groups. COMPLEXITY TUTOR was used to help students learn the topics of NP-completeness in algorithms classes and prepositional logic proofs in discrete math classes. Since this is the first significant study of using a computerized tutoring system in theoretical computer science, results from the study not only provide evidence to support the suitability of using tutoring systems in theoretical computer science, but also provide insights for future research directions.