The aim of the study is to analyze the factors that form dysfunctions in the provision of housing for orphans, to evaluate the effectiveness of regional measures of social support for graduates of residential institutions, which make it possible to partially compensate for the risks associated with their housing deprivation. The leading research method was a questionnaire survey of employees of guardianship and guardianship bodies (N=694). On a number of issues, the ratings obtained were compared with the opinions of graduates of boarding schools (N=3868). The research results illustrate the dysfunctions of the social security of orphans, the risks of housing deprivation at the “breaking point” of social support when leaving the orphanage and before receiving their own housing. The presence of these break points is typical for many regions of the Russian Federation and is due not only to insufficient financial resources, but to bureaucratic costs that limit the implementation of flexible models of provision of housing for orphans. The largest variation range between the assessments of guardianship officials and orphans is characteristic of such support measures as the provision of temporary housing and consulting assistance in its selection (in the first group of respondents, the share of positive assessments is 1.7 times higher). Insufficient staffing of guardianship and guardianship bodies, the maximum level of workload for each employee are an additional factor limiting the possibility of providing the necessary social support to orphans. In addition, the study identified individual cases of “reverse” social dysfunctions associated with dishonest behavior, and falsification of the status of an orphan.