This three phase longitudinal multiple-case study, framed by positioning theory, investigated how four novice teachers learned to use professional judgment in their literacy instruction. Data sources from coursework, student teaching, and novice teaching were included. Interviews, observations, researchers' observational notes, and school and classroom demographics were compiled and analyzed to create case reports. Findings indicated while they differed in their use of professional judgment as novice teachers, participants learned this skill in student teaching rather than in coursework, which caused us to question whether teacher preparation programs are preparing teachers to use professional judgment or training them for technical compliance.