Housing support is a service offered by municipalities in Sweden which aim to help people with psychiatric and/or neuropsychiatric disabilities to manage their daily lives, often in their own home. Housing support workers therefore have an important role in supporting people with psychiatric and/or neuropsychiatric disabilities. In certain municipalities in Sweden, housing support with a family-oriented approach has been implemented to help parents with parenthood and to structure their everyday lives with the family as a whole. This study aims to examine the possibilities and challenges that housing support workers face in their work with parents and families receiving family-oriented housing support. A further aim with this study is to understand the conditions that are created during interaction and in relations between the housing support workers and the parents, utilizing an analytical framework derived from concepts within the theory of social responsiveness. The method used in this study is based on semi-structured qualitative interviews with housing support workers working with a family-oriented approach. The empirical data has been analyzed through a thematic analysis, resulting in three main themes to present the result and analysis. The findings of this study show that there are both possibilities and challenges with their work taking place in the family's home environment, such as being where the everyday problems are being manifested, but also handling other family members. Results also show that housing support workers within a family-oriented approach deal with a bigger network as they have to manage the family as a whole. Other challenges were about keeping boundaries between their professional role and being seen as a friend or family member. The main result of this study is that social interaction and relation between the housing support worker and the parent that receives housing support is substantial and inevitable.