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This study was situated in an alternative high school using the critical self-reflections of six teachers working to reengage students enrolled at an alternative high school. The disengaged students in this case are identified as “compliant,” students who came to school every day yet failed to make sufficient credit-earning progress. This Action Research (AR) investigation was part of a larger study to analyze students’ struggles and barriers in completing high school. The study revealed the challenges, demands, and frustrations involved in re-engaging compliant students and the impact on teachers’ feelings of confidence in their re-engagement efforts. Expanding re-engagement interventions and creating intentional plans could boost teacher beliefs that they can influence student re-engagement and success.