Background/Context: As grounding for our work, we consider the creation and development of the teaching profession as a particularly "feminine" role. We then briefly describe the contemporary context of schooling, particularly related to neoliberal accountability and its impact on teachers' experiences. This comparison shows that the historical claims pertaining to women in the teaching workforce have modern-day equivalents, suggesting that the workforce and emotions pertaining to it are still heavily regulated and monitored. Purpose of Study: The purpose of this study is to explore how teachers' emotions are or are not supported and nurtured in an urban high school, contextualized by an exploration of what it means to work in a "feminized" profession that is increasingly subject to regulations that limit teachers' autonomy and agency. Research Design: Drawing on portraiture methodology and using interview and field note data from a case study on teacher morale in an urban high school, we advance a theory about the emotional rules of teaching in a neoliberal era. Findings: We argue that teachers have been socialized into the emotional rules of the profession in ways that inhibit their expressions of so-called outlaw emotions, or negative emotions that certain groups have been taught not to exhibit. For some teachers, these emotions may manifest as vulnerability, shame, or burnout. Conclusions/Recommendations: We conclude that emotional rules are embodied and that there are material consequences to the ways teachers are required to regulate their emotions. Teachers' expressions of outlaw emotions should be viewed as courageous. Teachers' vulnerability should be nurtured at both individual and institutional levels in order to build teacher community, reduce feelings of burnout and isolation, and ultimately (hopefully) reduce teacher attrition. Valuing the humanity and emotions of teachers is a critical step in ensuring humanity for all of our children.