The Swedish School of Library and Information Science has been offering dedicated courses in cultural heritage digitization since 2004. This paper describes the implementation of new assignments, projects and events in the courses that were developed since 2008. These new events include a critical image editing workshop, a text encoding enhancement of “dirty” OCR texts, experimental and critical evaluation of OCR software performance, and the design of a realistic digitization plan. The course innovations strengthen the course’s pedagogical legacy of sustainability and Dewey’s pragmatism, particularly of having the students perform hands-on work in digitization, experimenting with technology and drawing critical conclusions from the analysis of the results. To avoid some of the risks of naïve pragmatism however, the pedagogy and course design draws ideas from Lave’s and Wenger’s notions of situated learning by having the students engage in both local material with a situated relevance and testing their ideas in in particular existing communities of practice and/or expertise.