This study focuses upon youth shelters as non-profit, voluntary organizations, and their relationship with formal child welfare systems. Two case examples, Covenant House (CH) and Youth Without Shelter (YWS) are examined through archival material, participant observations of shelter culture, and structured/unstructured interviews with front line and managerial shelter workers. These methodological tools provide a distinct portrait of the evolution, the life stories, and the present day activities of two prominent Toronto youth shelters. The findings suggest that both Shelters operating goals have been modified in order to reach a suitable partnership with more entrenched and formal child welfare organizations (such as the Childrens Aid Society). CH and YWS were envisioned by their architects as alternatives and buffers from the impersonal and bureaucratic formal system. However, both Shelters are now increasingly described as dumping grounds for formal system players, and less of alternative havens or buffers. CH and YWS are currently crowded facilities predominantly harboring system kids rather than street kids. The consequences of such an arrangement are threefold: (1) CH and YWS no longer possess an internal environment to support traditional street kids; (2) Both Shelters no longer exist as short-term emergency crisis centers and have strayed from their original intentions; and, (3) Many shelter workers feel frustrated and impotent in working within this dynamic. Two distinct explanations for CHs and YWS transformation are discussed, as well, numerous recommendations are provided regarding the survival of such youth shelters.