Educational simulations represent a substantial innovation in the formal learning process, mainly due to their dynamic structure, interactivity, and complexity. Nevertheless, these features could arguably simultaneously problematise the adaption of digital simulations to “traditional” forms of teaching. Educational simulations not only provide a concrete methodical approach but also create new educational environments (“problem spaces”), generating additional sets of goals in other areas of learning (for example, in personal and social education), thus moving beyond the limits of classical history teaching. In a case study of the 'Czechoslovakia 38-89' educational simulation, we demonstrate how an educational simulation can extend educational goals from the reproduction of facts towards a deeper understanding of the multifaceted historical context. Stemming from a field survey that took place at 38 schools with more than 3500 students, this paper analyses the benefits and challenges related to the use of the above-mentioned digital simulation in the Czech formal schooling system and the acceptance of the simulation by Czech teachers and students. The study also describes how an educational simulation benefits students in terms of reflecting on witness accounts, illustrates the benefits of using constructed memory for education, and reflects the problem of the authenticity of witness accounts in historical education.