Leveraging digital technology for practice innovation is a compelling challenge. Limited education and training prevent human service practitioners from incorporating technology into practice. Progress in this area will be achieved when significant changes to pedagogy support technology integration with teaching/learning partnerships in higher education. With the recent attention to relational Child and Youth Care (CYC) practice in cyberspace (Martin & Stuart, 2011), this paper aims to highlight student/teacher explorations in this emerging area of clinical practice using student-driven simulated online counselling sessions supervised by the course instructor. Beyond critical learning within the roleplay activities, students engaged in solving disruptions to simulations, which can enhance their future agility in real practice situations (Rooney, Hopwood, Boud, & Kelly, 2015). Foundations in the Scholarship of Teaching and Learning (SoTL), experiential learning theory, and learner-led approaches guided student engagement with technology and reflexive practice in this graduate level classroom.