This study examines the effects of technology-assisted instruction with teacher prompts on the ability to visualize and solve fraction multiplication word problems for four middle school students with learning disabilities. A multiple-probe design across participants, a type of single-case design, showed a functional relationship between the intervention and the targeted mathematical outcomes. Although there were some fluctuations over time, students demonstrated improvements from the baseline to intervention phases (Tau ranged from .76 to 1.00 for visualization and was 1.00 for problem-solving). Researchers employed Bayesian cumulative link mixed effects models to examine the moderating effects of word problem question types. Students showed greater maintenance effects on problem-solving than on visualization tasks, as reflected in changes in level (logit coefficient = 2.6) and trend (logit coefficient = 0.22). Students and teachers perceived vocabulary and multiplication fact practices, as well as the cognitive and metacognitive features embedded in the technology-assisted intervention, to be useful in learning targeted mathematics concepts. This study underscores the role of technology integration in enhancing teachers’ instructional approach and in aiding students’ acquisition and retention of mathematical concepts and skills.