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Introduction: Learning and growth in postgraduate medical education (PGME) often require vulnerability, defined as a state of openness to uncertainty, risk, and emotional exposure. However, vulnerability can threaten a resident's credibility and professional identity. Despite this tension, studies examining vulnerability in PGME are limited. As such, this study aims to explore residents' experiences of vulnerability, including the factors that influence vulnerability in PGME. Methods: Using a constructivist grounded theory approach, individual semi‐structured interviews were conducted with 15 residents from 10 different specialities. Interview transcripts were coded and analysed iteratively. Themes were identified and relationships among themes were examined to develop a theory describing vulnerability in PGME. Results: Residents characterised vulnerability as a paradox represented by two overarching themes. 'Experiencing the tensions of vulnerability' explores the polarities between being a fallible, authentic learner and an infallible, competent professional. 'Navigating the vulnerability paradox' outlines the factors influencing the experience of vulnerability and its associated outcomes at the intrapersonal, interpersonal, and systems levels. Residents described needing to have the bandwidth to face the risks and emotional labour of vulnerability. Opportunities to build connections with social agents, including clinical teachers and peers, facilitated vulnerability. The sociocultural context shaped both the experience and outcomes of vulnerability as residents faced the symbolic mask of professionalism. Conclusion: Residents experience vulnerability as a paradox shaped by intrapersonal, interpersonal, and systems level factors. These findings capture the nuance and complexity of vulnerability in PGME and offer insight into creating supportive learning environments that leverage the benefits of vulnerability while acknowledging its risks. There is a need to translate this understanding into systems‐based change to create supportive PGME environments, which value and celebrate vulnerability. In this article, @heathermnichol et al. explore resident experiences of vulnerability and consider how to embrace the value of vulnerability while mitigating its risks. [ABSTRACT FROM AUTHOR]