This article explores and compares the impact of studying a challenging literary text at GCSE on pupils with and without learning difficulties. It is based on the findings of a qualitative classroom-based research project that analysed taped pupil conversations to measure the resilience of the response of secondary school students to reading Shakespearean texts. The data gathered from questionnaires and captured conversations in class suggests that pupils with learning difficulties become risk-averse in their learning because they do not want to experience failure. They demonstrate signs of resilience in their classroom behaviour but are often under-confident when working independently. Compared with students who are considered more academically able, pupils with learning difficulties find it difficult to negotiate the linguistic complexities of analytical discourse because it differs greatly from their own social lexis. These pupils are struggling to benefit from their encounters with challenging literature because they are not yet fluent scholars and are lacking opportunities to develop a confident critical voice of their own.