This study explored Metacognition and how automated instructional support in the form of problem-solving and self-reflection prompts influenced students' capacity to solve complex problems in a Web-based learning environment. Specifically, we examined the independent and interactive effects of problem-solving prompts and reflection prompts on college students' problem solving and writing within a Web-based instructional module. We found that students who received problem-solving prompts solved problems and wrote with more clarity than did students who did not receive problem solving prompts. Reflection prompts also positively influenced problem solving and writing, but only when students also received the problem solving prompts. This suggests that asking students to reflect on their work has a positive influence on students' problem solving, but only when they have clear understanding of what they are being asked to reflect on. Results are discussed relative to feedback and self-regulation theories. (Contains 3 tables.)