Mathematical Literacy was introduced in South African schools as a subject driven by life-related applications of mathematics. The design of assessment tasks for Mathematical Literacy (with its emphasis on real-life contexts) has created a new set of demands, not usually encountered in typical mathematics tasks. The purpose of this qualitative study was to identify and to explore how learners attend to some of the demands. In this study the context is understood in terms of attributes which provide the resources for the interpretation of the event. The study was undertaken with a class of 73 Grade 12 Mathematical Literacy learners. Data was generated from learners' written responses to a provincially administered trial examination as well as from semi-structured interviews with ten of the learners. The findings indicate that the learners displayed different levels of engagement with the contextual language, rules and reasoning required by the context. Some learners were also limited by their non-recognition of crucial information. It is recommended that assessment settings which provide learners with structured opportunities to engage deeply with the contextual attributes associated with different contexts should be encouraged. It is hoped that the findings of the study will increase the understanding of the nature and role of assessments in achieving the aims of Mathematical Literacy in South Africa.