This document discusses the development of a pedagogical design matrix for using information and communication technology (ICT) to promote boundary crossing in dual vocational education and training (VET) in Denmark. The research project examined challenges in connecting school and workplace learning in Danish dual VET. Interviews and observations were conducted with teachers, students, IT counselors, and workplace trainers. The findings were used to develop parts of a pedagogical design framework, including a matrix focusing on designing ICT-based boundary crossing activities. Critical issues discussed include the need to involve users in authentic experiments and to consider the plethora of ICT tools used in VET, not just pedagogical technologies.