The purpose of this case study is to demonstrate the challenges in conducting a multiple qualitative case study approach in a study that explored the communication experiences in the care of children with palliative care needs. This study employed a collective qualitative case study approach. It was conducted in three pediatric units in a Jordanian hospital. Each case comprised a child aged 1–12 years, their most involved family carer (mothers), physician(s), and nurse(s). Two data collection methods were employed, participant observation and semi-structured interviews, with three categories of participants: mothers, physicians, and the nurses who cared for the children that participated in this study (children were involved in the participant observation; however, they were not interviewed). I decided to avoid interviewing children in this study to avoid any potential harm to them. Within-case and cross-case analysis was undertaken in accordance with Stake’s recommendations. The within-case analysis focused on establishing the contextual background for every case. This was significant to protect the uniqueness of each case within its context and to be consistent with the case study approach. The within-case analysis was presented narratively for every case. Then, cross-case analysis was undertaken to systematically extract the themes and subthemes of each case to identify similarities, differences, and contradictions. The study was based on 15 cases, with a total of 197 observational hours and 60 interviews (conducted with 15 mothers, 12 physicians, and 21 nurses). This study is unique as it applies a qualitative collective case study approach that yields a rich and in-depth understanding of the experiences of communication from more than one perspective. It was underpinned by the interpretative constructivist approach that guided the analysis and accepts more than one interpretation of reality as viewed by the participants.