Middle school (MS) is an intermediary level of education between elementary and secondary school that typically includes students aged 10–15 years. There is limited research within the MS sport setting, particularly related to sport-related injury prevention. This qualitative study aimed to better understand the sport culture within MS sports and the communication strategies used among invested groups (i.e., athletes, parents, staff inclusive of coaches and school nurses). Semi-structured interviews were conducted with 19 athletes, 20 parents, and 18 staff (e.g., coaches, school nurses) from seven MS in two school districts during the 2018/19 and 2019/20 school years. Topics focused on understanding school- and sport-related factors related to education, safety, and communication. Analysis used a consensual qualitative research tradition, in which the research team discussed individually developed themes and categories from transcribed interviews, with the goal of coming to a consensus and creating a codebook. Throughout the coding process, the research team would reconvene to discuss coding decisions until consensus was reached. This study focuses on the themes of sport culture and communication. Dominant categories identified within sport culture related to participants noting why they were interested in MS sports, and their struggles with their perceived roles and engagement (e.g., helping parents stay engaged, finding coaches, oversight of school nurses). Competitiveness and safety could have conflicting roles and priority. Dominant categories identified within communication centered around limited communication between coaches and parents. Technological assistance (e.g., phone apps, websites) was available, but often varied by school and sport. Concussions were seldom discussed unless during the preseason meeting or when one occurred. Findings highlight that the MS sport settings may struggle with incorporating primary prevention into their cultures and ensuring reliable communication among individuals. Novel and tailored approaches to injury prevention are needed to help ensure buy-in and proper implementation.