Studies have shown that, to achieve a conceptual understanding of complex science topics, learners need to use self-regulated learning (SRL) skills, particularly when learning with Hypermedia Learning Environments (HLEs). Winne and Hadwin (2008) claimed that metacognition is a key aspect of SRL, particularly metacognitive monitoring and control. The aim of this study was to investigate the contingent relationship between metacognitive monitoring [e.g., judgment of learning (JOL)] and metacognitive control (e.g., strategy change) and whether those contingencies predicted learning about the circulatory system using an HLE. As a measure of contingency in metacognitive behavior, we examined the frequencies of learners' change in strategy use (i.e., adaptive), or lack thereof (i.e., static), when they verbalized a negative JOL. The results showed that the frequency of adaptive metacognitive behavior positively related to learning, and static metacognitive behavior negatively related to learning, above and beyond the effect of prior knowledge. These findings suggest implications regarding future research into SRL, as well as the benefits of helping learners to recognize the necessary contingency that follows from metacognitive monitoring when learning with HLEs.