Description: Vocational as well as teacher education show a growing amount of dual learning, ranging from apprenticeship and internship models (new and old) to more project and assignment oriented curriculum content. The main reserach question in the paper deals with new ways to connect learning and knowledge development in different school- and workenvironments. Methodology: The argument is based on a comparative analysis of cases studies in dual (work and school learning) professional education and workplace learning in two sectors. The first deals with student teachers in training schools, which combine workplace learning and theoretical study in their final examination assignments The second deals with expert workers in processing industry, which follow a dual course in proces engineering. This course combines high level practical assignments with learning complex science. In both studies qualitative (in depth interviews, analysis of work place learning diaries) as well as quantitative data (survey) are collected among students as well as organisations about opinions, learning experiences and learning results and about the relationships (or lack thereof) between workplace learning and school based instruction. Conclusions: An important conclusion is that the growing amount of work based learning in school based vocational and professional education poses new challenges to the way knowledge construction and transformation can be enhanced. Both on the level of content and on the level of guidance new connective practices are necessary. Another conclusion is that these challenges ask for new ways of communication and coordination between schools and workplaces (organisations).