The Supreme Court of Canada mandates recognition of systemic factors that create barriers for Indigenous peoples’ access to equitable justice. Specifically, R. v. Gladue directs courts to consider the unique circumstances of Indigenous peoples when engaging in decision-making processes in all criminal courts. Drawing from interview data with Indigenous and non-Indigenous defence counsel in Ontario, this study assesses whether and how Gladue factors shape bail hearings. Our findings reveal that the application of Gladue principles exists along a continuum, ranging from mere “lip service”, to the tailoring of bail decisions based on meaningful recognition of systemic disadvantages. We also highlight the importance of lived experience and representation of Indigenous legal actors and the challenges they encounter working within a colonial system. We situate these findings within broader critiques of risk-based bail frameworks and settler colonial legal systems, concluding with policy recommendations and directions for future research.