This paper will look at the experience of bad feelings and disappointments that arose despite the good intentions and generosity of providing pro bono treatment to foster children. Written in four segments by the founders of The Fostering Connection (formerly The Children's Psychotherapy Project, a program of A Home Within), the paper will explore the clinical, theoretical, and organizational aspects of this project. In the first part, we give a theoretical perspective followed by a report of some clinical work, and finally we offer some reflections on the development of our ideas to date including some thoughts about where we are headed. As psychoanalytically oriented psychotherapists, in the planning for this project we sought to bring our analytic point of view to the task of providing weekly psychotherapy to foster children and their families. For context, we will start by giving a description of how our organization works and a history of our ideas and evolution as a group.