Responsible leadership in schools is an ethics-based and human-centered approach to educational management that emphasizes committed, caring, and professionally value-driven decision-making. However, within the context of Iran’s educational system, the realization of such leadership faces numerous obstacles, the identification of which can contribute to the reconsideration of educational policies, structures, and programs. The aim of this study is to identify and explain the barriers and challenges that school principals encounter in fulfilling their roles as responsible leaders. This research was conducted using a qualitative approach, employing Charmaz's constructivist grounded theory methodology. The participants consisted of 12 principals from public schools in Kermanshah at the elementary, lower-secondary, and upper-secondary levels, selected through purposive sampling based on theoretical saturation. Data were collected through in-depth semi-structured interviews and analyzed in three phases of open, axial, and selective coding. The findings revealed that principals face a set of multi-level challenges in the process of realizing responsible leadership, which can be categorized into five main domains: individual challenges (such as the tension between ethical commitments and administrative demands, and role ambiguity), professional challenges (including the dominance of quantitative indicators and role uncertainty), interactional challenges (such as teacher resistance and conflicts with family values), cultural challenges (like authoritarian cultural norms and disregard for care), and structural–organizational challenges (including centralization and the absence of institutional support). These interrelated challenges weaken the space for ethical decision-making and render the path toward responsible leadership a stressful, exhausting, and at times conservative process.