This chapter explores fieldwork supervision in social work education as a generative space of professional becoming, where students do not merely acquire technical competencies but are invited to reflect on their ethical positioning, relational capacities, and emerging professional identities. Drawing on critical pedagogy, ethics of care, and post-structuralist perspectives on identity formation, the chapter argues that field supervision—particularly as enacted by field tutors—must be understood not only as a pedagogical or evaluative process but as a dialogic, embodied, and politically situated practice. Rather than treating supervision as a neutral function of training, the chapter foregrounds its role in shaping how students engage with ambiguity, navigate value tensions, and learn to think critically within complex institutional environments. Power dynamics, institutional cultures, and global challenges such as austerity, migration, and epistemic inequality all shape the supervisory encounter in ways that demand conscious reflexivity. Through a critical reading of international literature and reflections grounded in the Italian context of field education, the chapter explores how supervision can serve as a space of relational learning, affective containment, and epistemological negotiation. Particular attention is given to the role of the field tutor as a mediator between university and practice settings, as well as a co-constructor of ethical and decolonial orientations to social work. Ultimately, the chapter calls for a reconfiguration of field supervision as a transformative praxis—one that not only supports students’ learning but also contributes to the ethical and political renewal of the social work profession.