This paper discusses the design of an online digital participation campaign, developed as an academic research project in Singapore. In order to develop appropriate exercises which fitted the tool and the context, we addressed several questions: how can online participation tools maintain a negotiation and education power? What data generated by citizens, in the form of a design proposals, is useful for urban design? We created two different exercises, at different scales: one exercise asking people to design proposals with functional blocks and one where citizens could decide the equipment and furniture in a public space. For each exercise we discuss the scale, the elements, the educating and mediating impact, but also the way we intended to use the gathered local knowledge in urban design. The exercise did not receive the expected contributions, gathering little attention from internet users. More results were obtained using an offline experimental setup. In conclusion, we reconsider the weakest points of the design in a critical analysis and provide direction for future online participation tools.