Commencing with a presentation of theoretical perspectives on the judiciarization of social problems and public space, this article will illuminate the results of over a decade of research on the judiciarization of the homeless in Montréal, Québec. Utilizing methods to extract data from the municipal court in Montréal between 1994 and 2010, this research allowed for a comprehension of the extent to which, as well as the pathways taken by, contraventions (fines and tickets) are issued to homeless people in Montréal bound by municipal regulations and by-laws. In this article, we will present the growing evolution of the use of contraventions: spawning the reasons cited for the offences, the characteristics of the accused, and the contravention pathways deployed — ranging from their initial issue to the possible imprisonment for non-payment of a fine. Following the presentation of these results, we will demonstrate the negative consequences of this form of penalization for the persons affected (the homeless) as well as the criminal justice system.