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This study analyzes how two urban secondary school teachers supported their 40 predominately Latino and African American male students in making digitally mediated projects. It also examines how teachers developed new literacies in urban schools using design thinking processes. As a learning approach, design thinking allows students to make hands on projects that solve complex problems. Findings for this research reveal that despite the contrast in teachers’ backgrounds, which include their previous experiences with digital tools, both were able to support students in learning using digital technology. This work contributes to literature in urban schooling contexts by providing empirical data to support ways teachers might develop students’ problem-solving skills using digital tools.