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Trust is a critical ingredient to young people’s experience of effective learning relationships with youth program leaders. Youth’s trust typically follows trajectories that grow over time spent in a program through interactions with leaders. We interviewed 108 ethnically diverse youth (mean age: 15.7; range = 12–19 years) at 13 project-based programs (arts, leadership, technology) to obtain their accounts of experiences that increased their trust. Qualitative analyses were used to capture the specific, varied processes youth described. Findings identified 11 sequences of trust-growth, each entailing a distinct type of leader action in a specific context, leading to distinct youth evaluative processes. These fit into 3 overarching categories representing different types of youth experiences with the leader: (a) the leader provided support to youth’s work on their project, (b) the leader interacted with youth as a whole person with goals, needs and interests beyond the program, and (c) youth observed and evaluated leaders from a bird’s-eye view. Theoretical analyses across the processes led to 4 propositions about how youth’s trust grows. First, project-based programs provide rich and varied affordances for leaders to foster youth’s trust-growth. Second, trust-growth often stems from leaders’ attuned responses to situations when youth experience vulnerability. Third, trust develops when leaders’ actions align with youth’s goals and empowerment. Fourth, youth’s appraisals of trustworthiness involves discerning assessments of leaders over time; these included youth compiling evidence from multiple experiences and employing multiple criteria. The findings lead to recommendations on how trust can be cultivated in youth-staff relationships.