This article argues that homelessness in Calgary, Canada is entrenched, in part, due to a systemic cycle of exclusion and defensive tactics carried out by those who are homeless and employed. A major proportion of this systemic exclusion occurs via a number of societal institutions: the provincial welfare structure in place to assist those in need; the provincial registry system for identification and licensing; the banking system, employment service providers; and the civil society organizations that provide shelter. Through one-to-one interviews with employed people experiencing homelessness in Calgary (n = 61) we found four identifiers that contribute to maintaining the adverse situation facing those who find themselves homeless: security of, and access to, replacement identification; access to banking; access to a mailing address; and accessibility to stable, permanent employment. Without access to these elements re-establishing social inclusion and navigating the transition to stable housing and non-vulnerable employment is far more difficult.