The goal of this paper is to present four key assumptions regarding the measurement of cognitive and metacognitive regulatory processes used during learning with hypermedia. First, we assume it is possible to detect, trace, model, and foster SRL processes during learning with hypermedia. Second, understanding the complex nature of the regulatory processes during learning with hypermedia is critical in determining why certain processes are used throughout a learning task. Third, it is assumed that the use of SRL processes can dynamically change over time and that they are cyclical in nature (influenced by internal and external conditions and feedback mechanisms). Fourth, capturing, identifying, and classifying SRL processes used during learning with hypermedia is a rather challenging task.