Preparing teachers to work in urban settings poses unique challenges, as urban communities are complex and require systemic understanding of students and their families, culture, and community. Pre-service teachers often harbor misconceptions about what it means to work in urban settings and many bring to their teacher education program minimal first hand experience. The purpose of this qualitative study was to understand pre-service teachers' use of online journaling (or blogging) to contextualize, question, construct and transform their understanding of their initial field experience within an urban school setting. The study used critical discourse analysis to study 31 undergraduate students' blogs in an introductory course prerequisite to entering an initial teacher certification program. The findings suggest transformative shifts in the areas of developing confidence and observation skills, understanding the complexity of schools, developing concern for others, promoting democratic ideals and becoming a professional. (Contains 2 tables.)