This paper reports the opportunities and challenges faced by first generation learners, all of whom were designated as being from scheduled tribes and scheduled castes, accessing education in a rural community in the state of Maharashtra, India. The design of the research and the methods used for this child-centred study aimed to generate data to enable reflection on the real-life complexities experienced by children in this situation. Ten case studies based around individual children who shared common experiences were developed. These children had attended the local Zilla Parishad School (Government funded school) in the past and were enrolled at a Non-Governmental Organisation (NGO) funded school at the time of the investigation. The ten case studies focused on those antecedents, contextual factors, perceptions and attitudes towards education that had shaped the experiences of the children. Their personal circumstances, opportunities and challenges emanating from their social, economic, cultural and political environments are discussed.