There has been a recent shift in Europe towards empowering citizens to shape Digital Transformation and Future cities. However, current methods of participation are unsuitable or unhandly for many people. In this paper, we report on the DT4REGIONS platform, a web based platform to exchange knowledge, real cases and decision making to citizens through DTStories and DTSolutions. Investigating the extent of Living Lab methodologies while addressing barriers to participation in conceptualization. The research contributes to both Digital Transformation citizen involvement and planning future cities. The platform leverages citizen knowledge, allowing high level expertise interactions, encouraging citizens to reflect and comment on their environment. Taking a case study approach, the paper discusses the divergences in citizen participation on the decision making process, focusing the design and deployment of the platform to tackle those blanks, in a city and regional level, through a survey with 38 city or region administration leaders and a workshop with 50 experts. The paper discusses the potential of the DT4REGIONS platform to address more conceptual issues, based on real study cases and concludes by a discussion on how the degree of this participation might be.