This qualitative single-case study illuminates the significance of effective character education implementation during elementary school years as students transition into middle school. The researcher conducted the study in an American school that consisted of two divisions: K-6 lower division and 7-12 upper division. The lower-school division was a National School of Character winner. Data were collected via individual interviews with educators in both school divisions, one focus-group interview with lower-school teachers, and a review of documents and artifacts. Findings revealed distinctive key practices and processes based on the different roles of participating educators and shared key practices employed by all educators alike. Data also revealed multiple indicators of effectiveness in both school divisions. The researcher also highlighted the main challenges in the way of character education effective implementation based on participants' responses. The researcher concluded with recommendations for further study and final reflections.