This chapter introduces academic challenges that undergraduate students face during academic work as opportunities to teach students self-regulated learning (SRL) processes and problem-solving strategies. Academic challenges provide opportunities for learners to engage in deliberate regulation to address learning problems, and for researchers to study learners’ regulation (Hadwin, J¤rvel¤, & Miller, 2011). Winne and Hadwin's (1998; Winne, 2018) model proposed that SRL occurs in four loosely sequenced, recursive phases: (a) task perceptions, (b) goal setting, (c) strategic enactment, and (d) large-scale adaptation. Challenges afford regulation in any of these phases and particularly in phase three when goal progress is disrupted. When students detect deviations in their progress toward goals, they are engaging in self-monitoring; they have a learning problem to solve. This invites regulatory processes: Choosing a strategy, using a strategy, adapting a strategy, or taking a step back and changing attributes in another SRL phase. Adopting this perspective, examining the challenges students encounter and the ways they strive to ameliorate those challenges reveals information about their self-regulation. This chapter reviews current research on challenges in undergraduate learning and strategies students adopt to regulate these challenges. It concludes with important implications and directions for practice, focusing on supporting students’ development of, and proficiency in, self-regulatory processes.