Framed within researches underlying the appliance of digitisation in public administrations, this paper analyses the relevance of investigating barriers and enabling factors present in the “grey area” which ranges from the positive test of digital innovation trials to their generalisation in all the different bodies of a public administration. Having a double step of analysis, the research starts from a systematic literature review looking at how, digital transformation in the public sector, is considered and analysed in academic journals in order to look at how much failures and barriers about wide-spreading and diffusion of it were already investigated and depicted. Starting from the analysis of the literature review – in which it was found a lack of analysis upon the aspects we intended to investigate – we executed a qualitative case study upon three Italian local public bodies dealing with the full implementation of digitalised tools for the interaction with end-users and citizens in general. Findings seems to suggest that the actual wide-spreading of the implementation of a “new” tool thanks to digital transformation, requires years and it is not devoid of obstacles and costs, which should lead both researchers and practitioners to “reconceptualise” the analysis of strategies and efforts for the full implementation of a “smart” digital transformation in the public sector.