This article offers an insight into the context and practice of housing possession hearings in which a social landlord seeks a possession order against a tenant who is in rent arrears. Drawing on the findings of the authors’ empirical research supplemented by insights from the psychology of decision making this article questions whether judges are able to exercise discretion in a manner consistent with the fundamental demands of ‘procedural fairness’. What our findings reveal is that while the legal process requires judges to engage in compensatory decision-making, and this is what they believe that they are doing, the reality is that judges are likely to be relying on heuristics. This does not, however, arise from a refusal on the part of judges to engage in more deliberative decision making but, from the context within which these decisions are made. Characterised by information deficits, low levels of representation and time constraints, the practice of housing possession does not facilitate decision-making that meets accepted standards of fairness. In response, we put forward proposals designed to enhance the consistency, transparency and accountability of decision-making while recognising the current climate of reform and dwindling resources within the legal system.