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Large scale Information and Communication Technology (ICT) infrastructure utilization is the foundation of smart grid and smart market scenarios. Thus, power system exposure to ICT infrastructure contingencies is naturally increasing. The paper at hand focuses on those types of ICT contingencies that may potentially affect transmission level reserve requirements. The analysis indicates that these contingencies are characterized by large scale power outages at very low probability. The German 2020 power generation scenario serves as study case for integrating the resulting risk of ICT failure into the calculation of reserve requirements using the method of recursive convolution. Calculated reserves with and without consideration of selected ICT contingencies are compared. The paper highlights the need for ICT infrastructure concepts that aim at safety by design from the beginning. It concludes by summarizing identified `safety-by-design' criteria that merit further investigation.