This case study reports on a doctoral research project conducted in a school using critical discourse analysis to examine the discourse of youth ‘disaffection’. The study aimed to identify how some students acquired the label ‘disaffected’ and considered the extent to which the quality of relationships between teachers and students contributed to their disconnection from learning. Drawing on Norman Fairclough's (2003) approach to critical discourse analysis, excerpts from transcripts of a combination of focus group and semi-structured one-to-one interviews with six students, a teacher and a learning mentor were chosen for closer analysis, on the basis of their salience to the main research questions. Teachers' narratives largely attributed students' disconnection from learning to their cognitive, emotional and behavioural deficits or the negative influence of their peers. The young people's counter-narratives suggested that their disengagement was a rational response to a perception of de-motivating curricula and conflict with teachers, resulting in a counter school culture, where teachers' demands for conformity were met with resistance. The success of a creative writing and multimedia project pointed to the importance of building positive relationships between students and teachers to re-engaging students at risk of dropping out of school.