The 21st century city is faced with a myriad of social, political and environmental complexities. The increasing global urbanisation puts pressure on the various spheres of government as well as on citizens to continuously redefine and manage public assets and spaces – often built for social contexts that no longer exist. While top-down approaches have arguably failed to engage and motivate communities in meaningful ways, bottom-up initiatives have also proved difficult in promoting lasting impact on official policies. The democratisation of digital technologies provides new opportunities for citizens to organise themselves around local issues. These complexities galvanise communities around a civic debate about the present and future identity of the places they live in. Yet, it is still fairly challenging to balance community expectations, on one hand, with transparency regarding the complex decision-making processes inherent to public administration, on the other. In this paper, we present common approaches to placemaking. We then discuss new forms of digital placemaking and illustrate their application through four interventions we ran to investigate digital technology adoption for community engagement initiatives. Based on those scenarios, we investigate: (1) the shifting role of digital technologies as tools employed by individual groups to create placemaking initiatives, and (2) media interventions that inform and bring decision makers at the top, and citizens at the bottom together into more collaborative and focused city making efforts.