This qualitative case study discovered the experiences of urban high school teachers using gamification with students who have difficulty staying on task. Five research participants shared their approaches to classroom management and gamification, their insights regarding student on-task and off-task behavior, and their perceptions of the impact of gamification on students who struggle with staying on task. Data from surveys, interviews, observations, and artifacts revealed a variety of off-task behaviors that teachers aim to manage in their classrooms. Participants’ approaches to minimizing offtask behaviors and improving productivity involve addressing and overcoming the perceived underlying causes of the lack of student motivation and engagement. The study found teachers employ a broad range of strategies, including gamification, to manage their classrooms and maximize student on-task behavior. The findings show gamification is a key component of teachers’ classroom management to increase on-task behavior through impacting motivation and engagement. Participants perceive an improvement in student academic outcomes due to higher productivity resulting from student response to gamification. The results of this research suggest it would be beneficial to include gamification in classroom management training for urban teachers who work with students who have difficulty staying on task. A proposed classroom management training curriculum with gamification, based on the findings, is outlined herein.