Today, some Java program learning support systems have been proposed. Each student has his/her own learning level. It is important to give questions suitable for his/her learning level for each student. But it will cause an enormous burden to the teacher. In this paper, we implement the automatic generating function and the scoring function regarding debugging questions in Java programming learning assistant system called JPLAS. We proposed personalized learning with two functions such as automatic generating and scoring of debugging question used in JPLAS. We showed the effectiveness of proposed method with chi-squared test.