In an ongoing effort to address the needs of 21st century teachers, a service-learning project was designed which coupled structured reflection and technology. The reflective practitioner model through the use of traditional methods coursework has long been viewed as the most appropriate model for the development of teachers (Hall, 2012). However, deep reflection is difficult for most pre-service teachers, and is often viewed as assignments that need to be completed in order to successfully complete a course, instead of being viewed as a powerful learning tool that can be used to empower and engage in their own development (Stenberg, 2010). One way of evidencing this reflection and deep learning is through the creation of digital stories (Barrett, 2006). This case study presents the application and outcomes of a service-learning project between an urban university and an elementary school in which pre-service teachers utilized digital storytelling as a method for critical reflection and application of content methodology. The focus on the pre-service teacher's understanding of content skills, reflective inquiry and enhanced technology skills also supports the National Educational Technology Standards.