At the beginning of clinical practice, medical students face complex end-of-life (EoL) decisions, such as limiting life-sustaining therapies, which may precipitate emotionally charged moral dilemmas. Previous research shows these dilemmas may cause identity dissonance and impact students' personal and professional development. Despite the prevalence of such dilemmas, medical educators have limited insight into how students navigate these often emotional experiences. This study explores how medical students make sense of and deal with moral dilemmas lived during EoL's care. This cross-sectional qualitative study used thematic analysis (Braun and Clarke) to analyse interviews with 11 Brazilian final-year medical students. The interviews followed the drawing of a rich picture representing moral dilemmas experienced by medical students when engaging with EoL care. The reporting of this study follows the Standards for Reporting Qualitative Research (SRQR). Participants highlighted four main themes when engaging with EoL care: 'experiencing death', 'making decisions at the end-of-life', 'connecting versus detaching: an upsetting dilemma' and 'being transformed'. They described the emotional overwhelm of experiencing death and the uncertainty in navigating EoL decisions. The central moral dilemma faced was whether to connect with or detach from patients. This dilemma was lived in the context of a hidden curriculum that preaches emotional distancing as a coping mechanism. Developing the moral courage to overcome this barrier and choosing to connect became a transformative experience, significantly impacting their personal and professional development and reinforcing their commitment to patient-centred care. Connecting with patients in EoL care involves breaking cultural norms to establish meaningful connections with patients aiming for compassionate care. This process may lead to identity dissonance and also represents an opportunity for transformative learning. Educators can support this transformative process by legitimating students' connections with patients, teaching emotional regulation strategies, and leveraging personal experiences to foster trust.