Information Systems (IS) education deals with increasingly abstract and complex design challenges. Through digital innovation, the field continuously expands to new application areas. To develop design competence, students need to build up a repertoire of experiences enabling in-depth understanding of use context and design settings. Most students are young and have limited workplace experience.  These circumstances are challenging to IS education and teaching. In this paper we share experiences from teaching and designing IS education to be adapted to this situation. We propose three teaching strategies for bringing authenticity and contextual relevance to IS education; (1) teaching by doing together, (2) enable authentic experiences, and (3) critical formative dialogue.