This chapter aims to deepen our understanding of judgments in organizations. Whilst previous studies have underscored the situated nature of individual judgments exercised by e.g. leaders or managers, our research focuses on how judgments emerge as organizational responses to recurrently emerging moral dilemmas. Accordingly, the chapter studies a setting (decision practices in the English healthcare sector) where moral puzzles (to fund or not to fund healthcare for apparently atypical patients) demand ongoing attention and systemic handling. The chapter conducted (and present findings of) a focused ethnography of the ways expert decision-making panels in three health authorities confronted, engaged, and coped with morally perplexed situations. The moral perplexity there lay in that panels were called upon to prudently and demonstrably determine whether a particular patient deserved or not exceptional investment, when the healthcare needs and rights of all patients under the same health system were taken into consideration. By adopting a practice perspective, the chapter develops an analytical account of the effortful accomplishments (sociomaterial activities or intertwined “projects” in practice theory terms), which enabled the recurrent collective exercise of judgments in accordance with publicly recognizable moral expectations—namely notions of fairness. The main contribution lies in conceptualizing the work of rendering moral judgments as practical, organized pursuits possible and meaningful, and hence in complementing current “ecological understandings” of individual judgment-making in organizations.