Boys' (under) achievement is frequently on the agenda in the Nordic countries, like in other parts of the Western world. Theoretical explanations for their lower achievement than girls typically emphasise the dissociation between hegemonic young masculinities and school work. In this paper, we focus on boys' strategies for managing schools conflicting demands, using data from a recently completed Swedish ethnographic study of the discourses of gender and pupil achievement at school in various local settings. The analyses show that boys engage in a strategy of complex parallel positioning to master school demands and peer-group expectations; they appear to distance themselves from swotting yet, at the same time, devote themselves to schoolwork. This dual positioning needs to be accomplished over a short period of time at the beginning of the semester. The analyses point to the critical time sequencing, and reveal what seemed to be a carefully self-monitored process where boys' academic participation had to appear convincing to teachers but neither too long nor too intense to interfere with their peer-group interactions and positioning. The analyses also show teachers' appreciation of the boys who manage to position themselves well academically.