This chapter provides an introduction to the systems approach that developed around a ‘come-as-you-are’ entry portal shelter in Pinellas County, Florida, called Pinellas Safe Harbor. Residents of PSH have access to a variety of services onsite, including master case management intended to ensure that they are receiving the services and supports they need to move forward with their lives, mental health screening and counseling, limited medical care, education, job placement training, life skills training, beds and meals. The type of system developed around PSH, which is based on a continuum-of-care model, has become an attractive option for policy makers in Florida due to the reduction in the number of persons living without shelter, its cost effectiveness, and its integrated and coordinated service provision. It is especially attractive in areas where there is little or no political commitment to rapid re-housing or Housing First. The general scope of the system was initially designed by an external consultant, Robert Marbut, who had been hired by Pinellas County and the City of St. Petersburg in Fall 2010 to develop a countywide strategic plan to address street homelessness. Intended to help policy makers and practitioners make better informed decisions regarding options they have in renewing and developing a systems approach to homelessness, this chapter identifies a number of the challenges, including those involving faith-based organizations, the system has faced and a number of factors that have led to the system’s ongoing, if at times tentative, support by stakeholders.