With countries around the world reporting concerns about the sustainability and wellbeing of the teaching profession, attention is being paid to the emotional and affective elements of teaching. This chapter explores the emotion of guilt, through the lens of one teacher’s experiences in a high-accountability environment. Alice, our participant, expressed feelings of guilt at being required to work in particular ways due to standardised testing regimes. She described the ways her students were impacted by practices resulting from high-stakes testing and highlighted a disconnect between her own values and beliefs and the realities of teaching under these conditions. We analyse Alice’s story informed by the concepts of affect, care and demoralisation. These ideas allow us to tease out nuanced perspectives on the experiences of teachers under contemporary labour conditions. In doing so, we argue that Alice’s feelings of guilt are a consequence of the tensions between her values and beliefs about teaching when working within the reality of policy conditions characterised by competition and measurement. This is significant because while policymakers may tinker at the edges of current conditions while seeking to reduce stress on teachers, there remains a need to address the fundamental tensions inherent for teachers whose motivations do not align with what is expected of them in schools today.