This article examines how individual differences (giftedness) interact with learning contexts (favorite versus least favorite courses) to influence learning processes and outcomes. The findings show that gifted and typically developing students differ solely in their expectancies for success and grades among a large variety of measures, including motivation (goal orientations, expectancies, and values) and self-regulated learning (self-regulated emotions, behaviors, and cognitions). These results imply that the learning context can override individual differences. Through the lens of the integrated self-regulated learning model (iSRL; Ben-Eliyahu & Bernacki, 2015), the article discusses why there are contextual differences in learning. By bridging the literature on mastery goal structure and self-determination theory, it is proposed that learning contexts focused on development and self-progress (i.e., mastery goal structured contexts) lead to adaptive achievement outcomes because competing basic needs are satisfied, competition decreases, and resources for learning are freed. Given the importance of self-regulated learning, students should be encouraged to develop learning habits and strategies based on self-regulation, which should be considered a 21st-century skill that can be scaffolded by educators in formal and informal learning settings.