This chapter explores perils of bias and mundanity in urban teaching, and focuses deeply on the impact and unpredictability of discretion and micro-decisions in the endless and multi-faceted micro-moments of daily classroom life. The narrator presents fault-lines in teaching practices that fail to adjust to socio-political moments, and the ever-increasing dangers faced by urban students and their parents. The complexities of preparing urban children for structural biases and inverted roles of schooling and policing in neighborhoods subjected to poverty are held in tension with value-informed teaching. The importance of intellectual, personal, and creative connection to learning activities is explored and highlighted in experiences of teachers and students and the varied levels of stress that school environments induce in their participants. The contradictions in instructional time in light of the demands of layered expectations, standards, and mandates culminate in an inversion of authority and the empty justifications of authority. The complex humanity of professional and personal identities is demonstrated through an unforeseen interpersonal exchange that destroys previous assumptions about philosophy, pedagogy, and personality. Decolonial approaches prove minimal in the face of broader white-normative and American-value-informed hurdles to equity and community-responsive pueblo pedagogy.