In a study conducted in 2008–2009, 25 employed homeless women in Calgary, Canada, were interviewed to gain a better understanding of their pathways from homelessness. The data analysis uncovered a mix of personal and societal issues to consider and provides a framework for understanding the complexity of sociocultural factors that contribute to the vulnerability of users of services. In combination, these many sociocultural factors affected the participants’ personal exit from homelessness. The role of service delivery organizations in helping to identify vulnerabilities experienced by service users and respond to these issues in practice will have an influence on resolving social issues like homelessness.