This article argues in favour of a situated approach to understanding learning in practice at trade vocational school and at trade in vocational education. Boundary crossing is regarded as contributing to expansive situated learning by apprentices across trade vocational school and the trade. The purpose of the article is to show that the relationship between strangeness and legitimacy is central to situated learning across different contexts such as at trade and at trade vocational schools. The article draws on examples from a recent qualitative field study of learning among apprentices in the Danish vocational education sector.