Our previous work classified students according to several dimensions, such as by student learning style and attitude toward the study of law, and then examined how these various classifications related to attitudes exhibited by students toward learning support systems. In doing so, we were able to clarify differences in preference among student types in regard to learning support systems. In the present study, we continued that line of investigation by attempting to determine ways to provide tailored learning support systems to students who were classified according to multiple dimensions. An evaluation experiment showed that students who did not respond positively to learning support systems based on logical formulas and logic circuits were the same students who had been classified as unreceptive to two defined learning styles (information-gathering–focused and practice-exercise–focused) and who reported feeling that legal texts are both hard to read and difficult to understand. However, a subsequent survey of the same students suggested that by reexamining system functionality and making adjustments, such as by changing the order in which the systems are provided and the method in which information is presented on screen, it may be possible to optimize the systems to best serve each type of student.