Gamification in education is being used as a way to increase student engagement and learning. While carrying a big promise, little is known about how students with different personalities, specifically extraverts and introverts, are influenced by game elements and mechanics: knowledge that is essential to ensure that implementing gamification will not disengage some students. In two quasi-experiments performed in an academic course, students (n = 102; n = 58) were faced with the immediate feedback game mechanics such as points, rewards, and badges, and comparative feedback mechanics such as leaderboards and progress bars. The perceived playfulness from the implementation was measured and a Partial Least Squares (PLS) analysis was performed measuring the relations between these elements and the way they increase the perceived playfulness throughout the semester. A moderation analysis was performed examining how extraverts and introverts perceive each implementation. Our results show that in both cases there were significant moderating effects between game mechanics and perceived playfulness. More specifically, the effect of leaderboards on perceived playfulness was higher for introverts and was negative for extraverts, meaning that implementing leaderboards may disengage extraverts. These results are important for gamification researchers who are looking at how different personalities derive perceived playfulness, based on different game mechanics and to educators who plan to include game elements in their courses.