Transported from Great Britain across the Anglosphere and into the fledgling commercial centres of the Tasman world, larceny was a way of life for most colonists and not easily contained. The porousness of Sydney’s urban and rural landscapes was an additional provocation for the period’s criminal population to continue pilfering goods, to embezzle and abscond. The following account describes the spatial dimensions of pilfering’s relation to colonial power giving rise to more and higher walls around manufactories, worksite-based labour management practices, and intensified surveillance nearly everywhere. Sydney’s built environment evolved to incorporate functional responses to the deprivations of systemic thievery, although the building outcomes were only partly determined by panoptical planning because period understanding of property crime and how it might be prevented was also changing. The colonial architecture was productive of knowledge-power relationships serving to define labour and labouring subjects in novel ways. These contributed to an “aesthetics of pilfering” whereby the perception of thieving acts was contextualised relative to a new moral compass, oriented to detect varied classes of perpetrators, settings, and stolen goods.