Purpose The relationship between private tutoring (PT) and mainstream education is among the complex themes characterizing PT discourses in the literature. This study examined the complications of practices and processes in tutoring and schooling to elucidate different roles played by PT and its relationship with mainstream education. Design/Approach/Methods This study used qualitative data from a diverse set of 37 PT providers from the State of Maharashtra, India, to delineate their roles and explore their relationship with schooling in this context. Findings The classification of PT providers’ roles into complementary, accommodating, competing, and substitutive ones demonstrated a diverse range of relationships between PT and mainstream education. Further analysis showed that these relationships are dynamic in nature, and the boundaries between them are blurred. Originality/Value Research in the field of PT has been consistently pointing toward a perplexing mixture of positive and negative outcomes resulting from its relationship with mainstream education. This study transcended the positive vis-à-vis negative binary approach by contributing to the deeper understanding of PT relationships. Furthermore, it exemplified how future studies can disentangle the complexities of such relationships by deploying flexible, context-specific theoretical approaches.