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Privacy is a central issue in the digitalization of society and directly concerns all Internet users. Privacy education is part of the picture of a more just digital society: it aims at making users more aware of the importance of their data and of the technical and financial tools and processes that involve their personal data. Nonetheless, privacy education is confronted with a paradox: while people perceive the importance of privacy, they seldom take action to actually protect their personal data. iBuddy is a narrative simulation-based session inspired by research evidence about the privacy paradox and aims to (a) enhancing awareness and (b) promoting the uptake of privacy-safe behaviors for secondary and higher students (age range 11-20). The paper presents the design and development of the simulation and of the following modular debriefing, as a case study in evidence-based collaborative instructional design and in the instructional used of digital technology. The evaluation of iBuddy, which combined a post-session satisfaction and perceived learning survey (N = 978) and a follow-up survey (N = 124), provides insights in the novel domain of privacy education. Results suggests that iBuddy sessions are engaging, effective and conducive to medium-term behavioral change, thus indirectly confirming the design assumptions about how to tackle the privacy paradox through a simulation-based approach.