The importance of teacher dispositions has quickly become commonplace in the preparation of teachers. Unlike other well-established domains of teacher education, like knowledge and skills, the evolving concept continues to challenge those mandated to identify, nurture, and assess the dispositions of teachers. The purpose of this study was to expand the conversation on teacher dispositions by examining connections between perceived dispositions and dispositions-in-action using Argyris and Schön’s (1974) theory of action framework. Case studies of two experienced elementary classroom teachers working in high-needs urban schools provided information on how teachers perceive their teaching dispositions compared with dispositions evidenced in their classroom practices. Data for this multiple case study included a validated self-assessment disposition instrument, the Diversity Disposition Index, semi-structured interviews, and classroom observations. The study found evidence of congruence and incongruity between the participants’ perceived and observed teaching dispositions. While both teachers shared similar self-reported teaching dispositions, such an enthusiasm for content, importance of classroom management, and attention to expectations for students, their enactment of those teaching dispositions varied greatly in their classrooms despite similarities in context. Implications are provided for teachers working in high-needs urban schools who face unique challenges and for teacher education programs designed to prepare and support new urban educators.