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For the many struggling students who are new to programming, this type of objective feedback can be discouraging and may decrease their motivation to stay engaged towards success. To address this issue, this paper explores strategies for more effectively recognizing student progress on programming assignments and identifying small tasks for students to complete that will steer them in the right direction. Further, this paper will discuss a gamification approach for adding ``Daily Missions\" to Web-CAT, the Web-based Center for Automated Testing. 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To address this issue, this paper explores strategies for more effectively recognizing student progress on programming assignments and identifying small tasks for students to complete that will steer them in the right direction. Further, this paper will discuss a gamification approach for adding ``Daily Missions" to Web-CAT, the Web-based Center for Automated Testing. 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