Several studies demonstrate that Sport Education (SE) supports the development of an authentic sport experience. However, the ‘messiness’ attached to the reality of effectively enacting SE is less prominent in the literature. The aim of this study is therefore to capture the complexity, tensions and struggles (for both lecturers and undergraduate students) of delivering and experiencing an authentic Artistic Gymnastics (AG) SE season within learning communities. Action research framed this 13-week study. Participants included 33 undergraduate students, four lecturers (one experienced in SE and three experienced in AG) at a university in Brazil and a professor with expertise in teaching and researching SE who was contacted regularly throughout the SE season. Data were collected weekly and included: (a) weekly collaborative lecture group meetings after each class; (b) student reflective diaries; (c) lead lecturer weekly observations collected as field notes; (d) Facebook posts; and (e) student focus groups. Data analysis involved inductive process and constant comparison. Results conveyed: (a) the relationship of trust and interdependence between the lecturers who implemented SE; (b) how students created a safe environment that allowed them to overcome fear; and (c) how lecturers and students negotiated the different levels of students’ engagement during the season and the associated feeling of frustration. Lecturers and students developed into two separate communities of learners. Future studies should continue to examine the effectiveness of a community of learners within the SE context and specifically encourage lecturers and students to work together as one learning community, learning from, and with, each other.