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The goal of the current study was to characterize adaptive and maladaptive patterns of motivational change from the freshman through senior years of college using Self-Determination Theory. After identifying adaptive (n = 38) and maladaptive (n = 38) subgroups, we compared them on several indicators of academic and social functioning. Students in the adaptive trajectory group reported higher self-efficacy and overall higher psychosocial well-being than those in the maladaptive trajectory group. Semi-structured interviews with six students from each group explored the mechanisms behind change in motivation. Thematic analysis indicated that – although both groups faced academic challenges – the maladaptive group struggled to overcome them and experienced debilitating personal issues toward the end of their college careers.