Requirements for reasoning, explaining, and generalizing mathematical concepts increase as students advance through the educational system; hence, improving overall mathematical proficiency is critical. Mathematical proficiency requires students to interpret quantities and their corresponding relationships during problem-solving tasks as well as generalizing to different contexts; both requirements are particularly challenging for many students with learning disabilities. An in-depth review of research was completed to (1) demonstrate how interventions targeting mathematical problem solving are categorized into heuristic, semantic, or authentic approaches; (2) explore the degree to which generalization is presented in each approach; and (3) determine the efficacy of each intervention approach. Experimental studies (n = 17) demonstrating the effects of interventions designed to enhance mathematical problem solving for secondary students with or at risk of learning disabilities were analyzed. Findings indicate that the efficacy of the three intervention approaches varies, and that the real-world connections differ. Implications for research and practice are discussed.