The process of handling breakdowns in computer programming, a practice known as debugging, provides an auspicious context for fostering teacher-student communication about critical thinking. Toward this end, this chapter explores two practical classroom designs. The first design focuses on student journaling and art making about critical thinking processes and emotional experiences that undergird debugging. The second design focuses on instructors modeling and prompting for reflection on critical thinking strategies during debugging. These teaching strategies lead to growth in students’ impressions of their skills for handling failure and their confidence during failure, both vital components of environments that promote deeper learning.