Border and security studies have established that technologies are at the centre of the reconstruction of border spaces and border policing activities. The aim of this article is to explore the little studied domain of customs, that is, where border authorities are concerned with the traceability of goods and the movement of transport workers. Drawing on field research conducted in the “commercial” sections of five Canadian border crossings, we studied the concrete effects produced by the integration of surveillance and information technologies in the customs labour process. The article underscores how customs officers establish themselves as security actors, but also pays attention to the daily practices of border security professionals, as well as labour conditions and intra-organizational relations within border security agencies. Instead of increased efficiency, which the use of technologies ought to provide, this integration results in struggles between practitioners and middle managers due to deskilling and the automation of customs work.