This paper draws from a broader research project and reports on a qualitative multi-case study that investigated the learning experiences of seven Chilean teacher candidates during their practicum. The purpose was to know what they learned from students’ contexts during their clinical experiences and how they used that knowledge in their teaching. Semi-structured interviews, class observations, and documents such as portfolios and lesson plans were used as primary sources. Culturally Relevant Pedagogy (CRP) was used as the theoretical framework. Findings show that building strong relationships with students was the main vehicle to develop socially and culturally responsive practices. Three contextual components (type of institution, students’ backgrounds and diversity, and complexity and vulnerability of contexts) were identified as essential mediators for advancing a CRP approach. After providing insight on how the practicum shaped participants’ thinking and teaching in ways that embody CRP, the paper addresses implications for initial teacher education.