The significance of youth in the economic development of a nation is well comprehended, while the role of economic transformation in ensuring a successful School-to-Work transition for the younger generation has remained a solemn challenge, especially for the developing countries. Therefore, the objective of this study is to understand School-to-Work transition among the younger generation, considering key indicators of the Indian labour market during the post-reforms period. The findings implicate specific enigmatic changes in the labour market—despite decent economic growth, the declining labour force participation, declining employment and increasing unemployment across gender and sector persist as a significant challenge to a thriving School-to-Work transition for the younger population of the country. Youth—being the prospective human capital—remains highly vulnerable in the Indian labour market, and prospects for their transition in the labour market are skimpy and shrinking, while the challenges remain multidimensional.