This case report prepared for graduate students highlights issues to be considered before embarking on qualitative research projects, particularly those involving vulnerable people. I emphasize that qualitative research requires careful planning, respect for participants, an awareness of power imbalances, and strategies to provide comfortable spaces for participants to engage in the research process. I share insights from an exploratory project involving one-to-one interviews with women living in homeless shelters in Toronto, Canada, and women with serious mental health challenges living in supportive residences in that city. The objectives of the study were to understand women’s experiences and decision-making processes about cancer screening and to co-create with participants recommendations for improvements in health promotion strategies and the delivery of cancer screening services. Thematic analysis was used to analyze transcripts from 26 interviews. The case study reviews partnerships with community sites, practical aspects of interviewing, thematic analysis, preparing field notes, and issues of social responsibility.