This study informs the design and development of pedagogical agents that can flexibly support self-regulation by calibrating guidance to specific phases and facets of self-regulated learning (SRL) as individuals encounter challenges and develop more sophisticated understandings of the task and content. From a socio-cultural perspective of self-regulation, we examine the transition of self-regulatory control from teacher to graduate student during naturalistic instructional conferences. Three goals included (a) examining teacher-student dialogue about a complex task to see if fading actually occurs, (b) examining whether support and fading of support are calibrated to specific phases of the self-regulatory process at a given point in time, and (c) examining techniques used for scaffolding and fading scaffolding directed toward specific phases and facets (behavioral, cognitive, metacognitive and motivational) of the self-regulatory cycle. Findings support a socio-cultural perspective of SRL demonstrating a transition from teacher to student regulation across phases and facets of SRL. The paper concludes with an examination of how our findings can inform the design of computerbased scaffolds that can support SRL.Consistent with the goals of this special issue, this paper examines the evolution of scaffolding dialogue in face-to-face discussions. Our focus was specifically on the evolution of naturalistic teacher-student dialogue as it occurred in face-to-face instructional conferences early and late in an academic year. We wanted to understand how human agents strategically scaffold self-regulated learning (SRL). Specifically, we explore how learners and instructors monitor, regulate and appropriate control of student self-regulation of task understanding, goal setting/planning, strategy enactment, and reflective adaptation. Students in our study were charged with the task of developing a graduate level research portfolio that evidenced growth and competency in research methods. Rather than comparing the portfolios themselves, or the Instructional Science (2005) 33: 413-450 Ó Springer 2005