When students repeatedly reflect, it can enhance their metacognitive abilities, including self-regulatory skills of planning, monitoring, and evaluating. In a fluid mechanics course for undergraduates at a large southeastern U.S. university, in-class problem solving in a flipped classroom was coupled with intentional metacognitive skills instruction and repeated reflection to enhance metacognition. The weekly reflective responses were coded by two analysts to identify the recurring themes and uncover evidence of the development and/or reinforcement of self-regulating behaviors for academic management. To enable a comparison, a flipped classroom without the metacognitive instruction and repeated reflection was also implemented (i.e., non-intervention group). The two cohorts completed identical final exams. Based on our preliminary analysis with year one data, a statistically and practically-significant difference between the two cohorts was found with the free-response scores on the final exam in favor of the intervention cohort that had received the metacognitive support ( p < 0.0005; Cohen's d = 0.72). Also, the Metacognitive Activities Inventory (MCAI) indicated a significantly-higher positive change in self-regulatory behavior for the intervention cohort ( p = 0.001; d = 0.50). Focus groups were conducted to gather students’ perspectives on the reflective activity, with differences found by demographic group. In addition, a significantly higher proportion of females (versus males) viewed the reflections in a positive manner ( p = 0.05). Significant associations between themes in the weekly reflections and direct knowledge measures were also uncovered. This included a positive relationship between academic self-management (i.e., diligence and carefulness) and exam performance. Overall, our preliminary results point to a desirable impact of metacognitive instruction and repeated reflection on knowledge outcomes, metacognitive skills, and self-regulatory behaviors.