The purpose of this study was to explore the experiences and observations of marriage and family therapists (MFTs) conducting an empirically supported parenting program at a transitional homeless community. A diary method was used in recording five MFTs' observations and reactions to implementing the psychoeducational groups. Fifty‐one recordings were collected from three different parenting groups over the course of 20 weeks. Constant comparative method was used to identify themes related to MFTs' experiences of conducting the parenting program. These themes included the needs of at‐risk families, confidentiality, and role ambivalence and boundary ambiguity. We provide recommendations for best practices and an example of therapists' decision‐making process using Kitchener's () model.