Self-regulated learning (SRL) promotes both current and future academic achievement and must be adapted based on task demands. To develop SRL, gifted students must have opportunities to experience optimally challenging tasks. Gifted students' past experiences (or lack thereof) with challenging tasks affects how they approach current tasks, which affects how they will approach challenges in the future. The current study used a two-stage approach to examine the extent to which Honors College students are able to adjust their SRL approaches based on task demands. Stage 1 provided baseline data on which types of Graduate Record Examination data analysis problems each student found to be difficult or easy. Then, in Stage 2, students were provided individually designed, easy and difficult problems. The students reported their SRL processes while engaging with the problems. When students were solving difficult problems, they demonstrated lower self-efficacy, lower performance evaluations, and lower effort. Furthermore, students reported using more surface level strategies when solving a difficult task, compared with their deeper strategic approach employed when engaging with the easy task. These findings suggest that, although gifted students may be aware of deeper, more effective strategies, they may not transfer these skills to difficult learning tasks. Thus, one recommendation would be to provide gifted students with more opportunities to practice building and transferring adaptive SRL processes when faced with a challenging task.