We have developed environments that use teaching as a metacognitive, reflective, and iterative process to help middle school students learn about complex processes. We demonstrate that metacognition and self-regulation are crucial in developing effective learners and preparing them for future learning tasks. As evidence, we discuss the impact of metacognitive support on students’ learning performance and behavior patterns that promote better learning through selfmonitoring. Keywords. Metacognition, teachable agents, behavioral analysis.