A student's ability to regulate their thoughts, emotions and behaviors in the face of temptation is linked to their task specific motivational goals and dispositions. Behavioral tasks are designed to strain a targeted resource to differentiate individuals through measures of their performance. In this paper, we explore how student behavior on differentially gamed learning material relates to estimates of student motivational goals and dispositions. We leverage observations of students in two different courses using an intelligent tutoring system over an entire academic year. We use a previously validated heuristic model of gaming detection to label instances of gaming. Each student's tendency to game is estimated separately using highly gamed and non-highly gamed sections of the course. Each estimate of student gaming is compared to precourse self-reported measures of student motivations. Results indicate that in naturalistic settings, gaming on more challenging materials is less influenced by student motivations and potentially a result of adaptive learning behaviors. Similarly, student gaming estimates using only non-highly gamed material are significantly related to all targeted motivation measures. Implications and future directions are discussed. [For the full proceedings, see ED599096.]