The purpose of this study is to analyze whether five personality factors (extroversion, neuroticism, conscientiousness, agreeableness, and openness) moderate the impact of middle school students’ perceived parenting attitude on their achievement goal-oriented learning motivation. For this study, we conducted a hierarchical multiple regression analysis on the survey results received from 370 middle school students nationwide. As a result of the study, personality traits were found to have some significant moderating effects on parenting attitudes on achievement goal orientation. Extraversion negatively moderated the effect on parenting attitude on the mastery approach goal and positively moderated the effect of the achievement parenting attitude on the mastery approach goal. Neuroticism and conscientiousness appeared to negatively moderate the effect of rational parenting attitude on mastery approach goals. The results of this study confirm various aspects of the interaction between parenting attitude and personality characteristics in their influence on learning motivation. The cause of the phenomenon in which the influence of parenting attitude appears to be minimal or mixed in previous studies may be that parenting attitude does not have a consistent influence on children, but may act in complex and diverse ways through interactions with the child’s personality traits.