The issue of this paper is to explore what vocational knowing is made available for students in Swedish upper secondary vocational education (16+) within the Health and Social Care program, with a specific focus on literacy-related vocational knowing framed by contextualized teaching (previously integration of subjects). A case study of contextualized teaching in a Swedish upper secondary school was followed ethnographically during autumn 2012 in the Health and Social Care program (year 2 of 3). Cultural-historical activity theory was used for analyzing what vocational knowing was made available and what literacy aspects that contributed to this. Teachers constructed a theme, Death, in order to work with ethical content relevant for nurse assistants. Ethical dilemmas and literacy practices (writing notes, reading aloud) were used as tools for enhancing sharing of different perspectives. The object of learning was identified as the ability to change perspectives and taking the other’s perspective in a dilemmatic situation related to caring.