The Homeless Emergency Assistance and Rapid Transition to Housing (HEARTH) Act addressed the cruel and unusual punishment of the urban homeless under quality of life ordinances by requiring constructive alternatives to criminalizing homelessness. As enforced, these quality of life ordinances move homeless and poor people about cities and downtown areas. San Diego's St. Vincent de Paul Villages granted access to its 2008 biopsychosocial assessments to evaluate relationships between risk factors for homelessness and criminal interventions. Spearman's r was used to evaluate whether there is an association between the percent of the respondents' lifetime her or she spent homeless, and the number of times the individual was jailed. There is a positive, though moderate, correlation between the percent of lifetime her or she spent homeless and the number of times her or she was jailed (r = 0.34, p = 0.001). To ask what puts homeless individuals at risk for criminal intervention, a step-wise logistic regression model and Wald criteria were used to describe how risk factors for homelessness and incarceration are associated with the incarceration of the homeless. Days of drinking annually (B = 0.002) and low education attainment (B = -0.117) both contribute significantly to the likelihood the homeless respondent had been incarcerated (p < 0.05). Where other risk factors are present, and a profile or sub-population is more vulnerable, one episode of jailing could initiate a career of homelessness, or a single but enduring episode of homelessness.