In the Province of Québec, the phenomenon of imprisonment for non-payment of fines is the result of many social, political and legal factors, including systemic prosecution of people experiencing homelessness. Through the examination of grossly disproportionate sentence of such imprisonment, this article explores the possibility of demonstrating that this type of sentence is a cruel and unusual punishment or treatment under section 12 of the Canadian Charter of Rights and Freedoms, particularly due to the lack of individualized sentencing on the part of the trial judge. The consequences of this type of imprisonment are significant for the lives of people experiencing homelessness because it can increase their vulnerability to the criminal justice system and limit their social reintegration.