Field education provides students with the opportunity to supplement classroom learning with the hands-on practice needed to be successful after graduation. However, in recent years, field education has encountered several challenges including a changing societal environment, placement scarcity in the face of increased enrollment, and strict guidelines for the provision of adequate supervision. In response to these challenges, semi-structured qualitative interviews with 35 social work field education coordinators, directors, faculty liaisons, field instructors and field supervisors were conducted throughout the prairie region of Canada between July and December of 2020. These interviews were aimed at determining innovative, promising, and wise practices that would address the various challenges in the provision of field education while also providing a pathway forward to the transformation of more sustainable social work field education practices. Findings indicate that there is a need for additional supervision strategies and increased flexibility within field placements, as well as a greater focus on the need for decolonization within the social work field education sphere. The emergence of COVID-19 was also discussed as both an exasperating factor within the current field education system while simultaneously creating an opportunity to reevaluate and restructure current field education practices.