This paper presents a curious case study of a teacher in an informal media literacy learning environment who worked with a group of 9-year olds in Philadelphia. Using a mix of direct observation, interviews with the teacher and students, videotapes of classroom activity, examination of documents created by the students, as well as lesson plans and reflective writing produced by the teacher, this paper documents the experience of a novice teacher who, flummoxed by an accidental encounter between her students and a homeless person, transformed an uncomfortable the experience into a teachable moment. Children’s questions about homelessness became the organizing frame for the learning experience, as the instructor helped children make sense of information on the Internet, analyze popular culture films and news media, and conduct interviews with community leaders and advocates for the homeless. The inquiry process resulted in a collaboratively-produced multimedia project, created by children. The project included a 14-page nonfiction comic book, created with a digital camera and simple multimedia production software, that was shared with their families, civic leaders, and the school community. This paper demonstrates how teacher openness to unpredictability plus a high level of strategic risk-taking enable the construction of powerful learning experiences in work with city children. The case study has implications for pre-teacher education for digital and media literacy, including the function of support systems including in-school mentoring, reflective writing and peer-teacher support groups as they may promote the development of openness to unpredictability and strategic risk taking, which are conceptualized as a set of socio-emotional and experiential competencies that teachers need when using digital media in an urban community as a tool for learning.