Homelessness and related community ailments have plagued society for a number of years, and governments have found it difficult to get these under control. The sheer number of homeless with mental health afflictions and problematic substance use problems leaves no doubt about the need for a stronger, more urgent government response. Community ailments such as these have led to increased crime rates and incarcerations and overcrowded prisons without a lasting solution in sight. This chapter uses the transformative justice model, with the expectation it produces better results than current models, by examining the source of homelessness, mental health afflictions, and problematic substance use and their bi-directional relationship with crime. This inter-jurisdictional study compares the current situations in the state of California and the province of Ontario, which have a high percent of homeless populations. It proves that special attention to vulnerable populations such as racialized groups, the socioeconomically disadvantaged, and youth is warranted.