This chapter examines how the intra-action between Joan Tronto’s notion of “caring with” and Bracha Ettinger’s “matrixial wit[h]nessing” generates new possibilities for building trust and solidarity within pedagogical praxis in South African higher education. Proposing care as a relational practice, Tronto offers the moral element of “caring with” to highlight how caregivers and care-receivers are mutually, albeit asymmetrically, implicated. The notion of “caring with” resonates with artist/theorist Ettinger’s concept of care-carriance, as a space and a practice that invites and evokes the possibility of trust after the end of trust as well as her notion of aesthetic wit[h]nessing that emerges out of her matrixial theory of trauma, aesthetics and sexual difference. Ettinger proposes wit[h]nessing as a “being with” and bearing witness to the trauma of the other without engulfing the other. Instead it offers compassionate response-ability that risks vulnerability yet does not give way to assimilation with the other. Given South Africa’s traumatic past, this theory offers helpful insights for pedagogical praxis in which response-ability becomes key to building trust and solidarity within the learning environment.