Amidst a widespread turn to data analysis and automated screening in security contexts, the question of how decisions are made at the interface of embodied humans and algorithmic processes becomes pressing. This paper is concerned with the production of security decisions at the data border. It makes two contributions. First, it presents qualitative fieldwork amongst data processors at a European smart border targeting centre and, second, it traces a largely obscured cultural history of discretion as means of reflecting on the politics of contemporary data-led decision-making. Discretion is an important concept in contemporary administrative contexts, referring to a decision about the (non)application of a rule in contexts of public power and authority. Its etymon, discretio, however, referred historically to spiritual and visual discernment, as well as prudence and humility. I present the history of discretion to make two arguments: 1) decision-making at the data border is an uncertain visual practice oriented to seeing and authorising what is there and 2) discretion in contemporary data-led contexts revises the conventional ethical relationship between general and particular that has always been intrinsic to discretion. My overall point is that contemporary debates about judgement in automated security decisions are the most recent manifestation of long-standing tensions between rule and judgement, authorisation and uncertainty.