The Indian Institutes of Technology (IITs) are renowned for producing world-class engineers, executives, and entrepreneurs through their rigorous academic curriculum, internships, and placement opportunities. The admission into the various departments in the IITs is based on the ranks obtained by the aspirants by ‘cracking’ the Joint Entrance Examination (JEE) Advanced examinations. Being one of the most challenging entrance examinations in the world, the IIT aspirants engage in intensive training and coaching in addition to their regular school curriculum. Although hard work and consistent efforts help them win the accolade of being an ‘IITan’, the impact on the mental health of these aspirants remains overlooked. Hence, the current study is a qualitative inquiry to explore the challenges faced by IIT students in their JEE preparation days. We conducted in-depth semi-structured interviews with seventeen undergraduate students currently enrolled in an IIT. Inductive thematic analysis of the interview narratives revealed five themes, a) excessive weightage on the ‘IITan’ identity, b) psychological distress (parental, structural, self-imposed), c) guilt, d) upward social comparison, and e) motivation, that affected the mental health of the IIT aspirants during their JEE preparation. The results of the study indicate that although rigorous preparation resulted in academic success, it had a negative impact on their mental health. The results of the current study highlight the need to reform the coaching-preparation system considering the mental health of the aspirants. The findings emphasize the need for effective and accessible mental healthcare for the aspirants.