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This paper introduces a new perspective to recognize the urban social innovation executed by researchers and initiators as Urban Trojan in the urban system. It analyses different approaches taken by researchers/initiators to overcome barriers between the public authorities, the community, and the initiators/researchers themselves to execute urban solutions to societal problems. The analysis adopts three approaches to deal with the public authorities presented by Jessy Marsh, the editor of the “Citizen-Driven Innovation” guidebook of good practice on open and participatory approaches to bring citizen-driven innovation to policy makers. This paper metaphorically titles Marsh’s approaches as: working in shadow, depending on a hero, and infiltrating through cracks. Considering these approaches, this paper analyses four different interventions in deprived areas in Egypt. The paper analyses the approach taken by each intervention to deal with the public authorities in relation to their effectiveness and sustainability. Its effectiveness in terms of dissolving boundaries between the different sectors and sustainability to reproduce or open the way for other initiatives to take place. This paper targets generally researchers who work in developing countries in which the system responsible for the urban development is rigid towards urban social innovations. On a local level, it targets Egyptian researchers and initiators concerned with the urban field