The present research aims to explore and understand the issues of transition and retention of tribal students in Palghar District, a region that has a high density of ST population and is characterized by poor socio-economic conditions. In spite of initiatives like SSA and RTE, issues of discontinuation and low rates of transition are still a problem. It is hoped that through this research, a critical analysis of factors that influence educational discontinuation will be made and suggestions will be put forth that are context-specific. The research design for the study is exploratory and descriptive in nature, using a mixed approach. The primary data was collected through interviews/surveys of 58 students, 58 parents, and 37 community members, whereas secondary data was obtained through UDISE+ reports and government publications. The research revealed that the dropout rate is rising in the range of 5-7% in primary education, 10-12% in upper primary education, 18-20% in secondary education, and above 20% in ST students. Similarly, the transition rate is declining in the range of 85-90% in primary to upper primary education, 60-65% in secondary to higher secondary education, and 40-45% in higher secondary to degree education. The most significant factors affecting the dropout rate are poverty (25%), seasonal migration/labour (20%), lack of access to schools (15%), etc. Moreover, the research concluded that the dropout rate varies significantly across educational levels using the Chi-square test, as χ² = 9.72. In the end, the research concluded that it is essential to develop specific interventions for the education sector to address the gaps in the education system for tribal students.