As a black South African student from a disadvantaged background, my journey through doctoral studies at a historically white university revealed the complex, simultaneous dynamics of humanising and dehumanising processes within supervisory relationships. This autoethnography examines how supervisory relationships operate within contested institutional terrain, challenging linear transformation narratives through Ubuntu philosophy and Kronenberg's humanisation-dehumanisation continuum. Through analysing 25 of my personal diary entries spanning four years of my doctoral degree, I trace five interconnected themes that reflect the negotiation of contradictory institutional dynamics within academic spaces. The findings reveal how spatial negotiations, epistemic tensions and institutional fragmentation coexisted with authentic mentorship, safe space creation and strategic agency development. Rather than a linear movement from exclusion to inclusion, I experienced ongoing navigation of spaces marked by constraint and the possibility for agency. My supervisors' humanising practices operated within rather than external to colonial structures. This supervision exemplified Ubuntu's relational ontology where authentic relationships emerge through rather than despite contradiction and tension, enabling strategic navigation of institutional contradictions through accumulated relational practices.