Belarus and Ukraine embarked on digitalisation relying on an international experience. Ukraine experienced difficulties in building infrastructure and connecting their regions and faced challenges in providing training and raising citizen awareness on advantages of the digital services. Yet, the digitalization reform proceeded from the principles of citizen-centeredness and e-participation. Belarus, on the contrary, was quick in building the basic infrastructure and training their public officials. However, the e-government was oriented rather on technical aspects and inter-sectoral communication, than on the needs of the citizens. Despite the differences in both cases, the level of trust, the basic prerequisite for the quality e-services, has been low (Ukraine) or non-existent (Belarus). This paper uses multi-method approach to examine citizen trust and their adoption of e-services in developing political or administrative regime contexts that are characterized by low trust, variable digital literacy, and variable access to information. A key finding is that in both countries it was the historical legacy of access to free services, that was one of the barriers to building a sustainable and reliable system of e-services. However, while Ukraine started to improve their infrastructure and building trust towards digital services during the COVID-19 pandemic, in Belarus the authorities’ ineffective management of the pandemic has led to sharp decrease in trust towards authorities. As a result, rudiments of an alternative system of public-services’ delivery, based on the people-to-people model, have been launched by the civil society.