Task understanding is theorized as a critical aspect of effective learning, but its role in self-regulated learning and overall academic performance has been understudied. Research to date indicates that students with adequate task understanding perform well. However, these studies have not demonstrated what practices are needed for developing task understanding, nor do they explain the mechanism by which task understanding influences academic performance. We propose that the positive impact of task understanding practices in academic performance can be explained through students' experiences of academic challenges. This cross-sectional mediation study investigated whether a collection of academic challenges (i.e., metacognitive, cognitive, motivational, goal and time management, social and emotional, and initiating and sustaining engagement) mediate the relationship between task understanding practices and academic performance. Findings indicate that task understanding practices positively predict semester GPA, and cognitive and metacognitive challenges significantly mediated the relationship between task understanding practices and semester GPA. Our results suggest that task understanding directly contributes to academic performance; and that students who engage in task understanding practices are less likely to experience certain types of challenges and thereby are more likely to perform well academically.