As a result of the new discussion on sustainability generated by the United Nations (UN) Sustainable Development Goals and the European Landscape Convention, there is growing interest in participation as a critical ingredient in creating resilient, cohesive communities (UN 2015). Our understanding of participation is limited, often, to seeing it as a consensus-building tool or as the means to share relevant information with stakeholders. In this context, digital technologies are widening the range of people involved in decision-making, but they are seldom used to shift people’s values and beliefs and promote co-creation and collective creativity. This chapter investigates the recent evolution of the use of technologies in supporting democratic and transformative landscape planning processes. It sketches a framework for understanding the qualities of good digital participation, which it tests against four international case studies of participatory digital platforms, analyzing their potential to empower collective decision-making, strengthen civic discourse and identity, and foster the joyful unleashing of collective creativity. The cases reveal that digital participation is far from achieving its full potential to be more meaningful, engaging and, ultimately, transformative for those involved.