The notion of 'insurgent citizenship' has emerged as a critical concept to highlight the insufficiencies of the modernist liberal citizenship project. Referring to the 'everyday practices' of disenfranchised communities, it holds particular resonance in the urban context, and represents a range of formal and informal practices employed to claim for missing entitlements. Nevertheless, this notion is imbued with a certain ambiguity, and insurgent practices have manifested in a diversity of approaches ranging from contestation to negotiation-based practices. This is evident in the insurgent practices of Muungano wa Wanavijiji, a federation of the urban poor within Nairobi, Kenya, and a member of the Shack/Slum Dwellers International (SDI) network. This paper explores three key tensions experienced by the movement, which navigate trade-offs between: The development of a strong representational body and respect for internal diversity; strategies that can influence and contest hegemonic practices while resisting co-option; and mechanisms of engagement that generate immediate and material benefits while also pursuing structural change. Reflecting on these tensions, the role of negotiation and contestation-based practices in claiming substantive citizenship rights in Nairobi is explored. The case highlights the shifting complexity of insurgent citizenship practices that necessitates a deeper examination and disentanglement, exploring the contextual tensions and trade-offs insurgent movements face to obtain entitlements within the city. © 2014 Taylor & Francis.