By probing into the Strategy regarding the digitalization of education in Romania updated in 2021 by the Romanian Ministry of Education and Research after the COVID-19 and aligned with the latest European Digital Agenda for 2020-2030 published by the European Commission, we are hoping to offer future researchers a set of propositions to continue the inquiry on possible opportunities derived from emerging risks associated with the digitalization. This exploratory case study aims to identify a positive application of the risk filter that is capable to assess not only the range of risks, but also their systematicity, while planning a governmental digital strategy in a critical system like education. We believe that this topic deservers immediate attention, because of the unique opportunity offered by the COVID-19 pandemic, and because a good implementation plan is one of the strongest predictors of a successful strategy. As researchers, our hope is that by understanding the systematicity of risks which could influence the implementation of digital strategy in the education system in Romania, policies and programs can be developed further based on risk analysis and correct prioritization of operational plans. This research was an exploratory case study in which a digital strategy was analysed, and the characteristics of systemic risks have been mapped to the operational plans. It was concluded that the systematic filters identified for the risks could be used for planning the projects, to identify areas of risk exposure during planning and at various stages during the preparation of projects. The final outcome of the case study is that the identification of systemic risks can help with the management of each project and could lay the foundation to a project database.