This article examines how educational transitions in Hong Kong are concurrently classed processes and practices, and how learner identity is developed and negotiated in an education system that prizes English as capital. Through the lens of habitus, the connected but distinct autobiographical accounts suggest that the stronger the insulation between the home and the school, the keener an individual's sensitivity may be towards class distinction in adapting to a new field. Learner identity associated with academic success is potentially negotiable and self-sustained through determination, self-regulation, and reflexive strategies, rendering the availability of resource support less important for working-class students' identity development.