Legal restrictions on vagrancy and day labour in Iceland became increasingly strict in the seventeenth and eighteenth centuries, culminating with a decree in 1783 which prohibited any form of masterless labour and proscribed compulsory service on a yearly basis for most people over the age of eighteen. Despite strict regulations and the strenuous efforts of various state officials to uproot the problem, vagrancy and day labour remained relatively common and publicly acknowledged throughout the nineteenth century, thus highlighting the contrast between normative prescription (such as law) and everyday life and the ambiguity of power relations in rural Iceland, underscoring their contested nature. This article discusses how vagrants and illegal day labourers in Iceland in the early nineteenth century found ways to evade the authorities and make a living for themselves on the margins of society. It stresses the agency of the working poor and highlights some of the survival strategies employed, including passport fraud, the careful exploitation of cultural notions of hospitality and methods of earning social capital by providing useful services. The article builds on the case of a travelling healer and vagrant named Árni Sveinsson who was found guilty of vagrancy, forgery and quackery in 1821. His trial provides rare insights into the tactics employed by those on the margins of the law to get around undetected.