Caste-based discrimination is a significant issue in both the Indian and Indian-American diasporic contexts. In this paper, I explore the complex dynamics surrounding caste discrimination and its justification that manifests within educational institutions, in India. The study employs a multi-faceted approach, encompassing a literature review and consolidating previous works to show how the recent discrimination flows from India to the US, secondary data analysis, and survey questionnaires to provide a comprehensive exploration of caste-related discrimination within educational contexts, with a particular emphasis on first-generation Indian-Americans who may not have had direct exposure to the Indian discourse on caste in India. The findings provide valuable insights into the perception and recognition of upper caste identities caste, who explicitly state the relevance of the ethos and the enshrined principles and right in the Constitution of India-an independent, sovereign, postcolonial modern India, curate their caste-blind and caste expressions based on the complex interplay between caste identity, notions of merit, and social stratification. In addition, the findings also shed light on the dynamics of caste privilege and its relationship with mobility and educational/economic opportunities in a transnational context. Overall, these findings highlight the need for a more nuanced and comprehensive approach to address the multifaceted nature and impact of the reservation policy in educational institutions and in the US.