Recent research efforts have established that self-regulated learning (SRL) is necessary for teachers to attain successful professional development. Our study addresses two central questions: under what conditions in preservice teachers' education can SRL processes be enhanced to the optimum level, and how can we assess these processes? The participants of the study were ninety-seven preservice teachers, who were engaged in real-time teaching in a video-digital Microteaching environment. Each participant was randomly assigned to one of two groups: reflective support (RS) for SRL or no support (NS) for SRL. Participants in the RS group were explicitly exposed to SRL aspects and were directed to address these aspects in their reflective discussions of the teaching experience. The SRL process was measured as an online event during real-time teaching exercises, based on a coding scheme developed for this study to identify and assess the SRL skills by two major aspects: metacognition (planning, information management, monitoring, debugging, and evaluating) and motivation (interest and value, self-efficacy, and teaching anxiety). Results indicate that the RS group outperformed the NS group in all SRL measures. Implications for reflective support for SRL and event measures of real-time observations of preservice teachers' SRL are discussed.