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After more than a decade of e-participation initiatives at the urban level, what remains obscure is the alchemy—ie, the “arcane” combination of elements—that triggers and keeps citizens’ involvement in major decisions that affect the local community alive. The Community Informatics Lab’s experience with the Milan Community Network since 1994 and its two more recent spin-off initiatives enable us to provide a tentative answer to this question. This chapter presents these experiments and looks at election campaigns and protests as triggers for (e-) participation. It also discusses these events as opportunities to engender more sustained participation aided by appropriate technology tools such as software that is deliberately conceived and designed to support participation and managed with the required expertise.