Considerable research has examined the use of rapid guessing measures to identify disengaged item responses. However, little is known about students who rapidly guess over the course of several tests. In this study, we use achievement test data from six administrations over three years to investigate whether rapid guessing is a stable trait-like behavior or if rapid guessing is determined mostly by situational variables. Additionally, we examine whether rapid guessing over the course of several tests is associated with certain psychological and background measures. We find that rapid guessing tends to be more state-like compared to academic achievement scores, which are fairly stable. Further, we show that repeated rapid guessing is strongly associated with students' academic self-efficacy and self-management scores. These findings have implications for detecting rapid guessing and intervening to reduce its effect on observed achievement test scores.