Masters of Art / Cohabitation families have become a widely accepted and increasing form of family structure nowadays. However this family structure’s characteristics have caused it to be described as a risk factor to child development as it is associated it with negative child outcomes especially during the adolescence period. The adolescence stage itself has been described by literature as a unique human development stage coupled with a variety of physical, cognitive, social and emotional changes, making it a vulnerable stage characterised by experimenting with risk behaviours. Therefore the aim of this study was to explore and describe the challenges of cohabiting families with regard to discipline of the adolescents. An explorative and descriptive research design grounded in a qualitative research approach was used. Two set of data, namely (a) cohabiting biological parents, and (b) adolescent children living in cohabiting families, were collected for a better understanding of the situation. The population for the study encompassed all cohabiting parents and their adolescent children living in the city of Cape Town, and research participants were purposively selected from the caseload of Cape Town Child Welfare. Data was collected by means of individual interviews with the aid of an interview guide. Interviews were transcribed verbatim and field notes were taken. Data analysis was conducted according to Tesch (in Creswell 2009), and ethical considerations, such as confidentiality, voluntary participation, informed consent from parents and informed assent from adolescents, as well as no harm to participants, were adhered to. Most participants identified with cohabiting step-parent families. The reported challenges affecting discipline of adolescent children stemmed from poor parent-child relationships, ambiguous step-family roles, negative family communication patterns, and the applied disciplinary methods in cohabiting families. With consultation from some of the suggestions put forward by all the participants, the researcher concluded the study with recommendations for social workers working with cohabiting families.