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Gangs’ ability to exert territorial control in El Salvador is changing the social dynamics in marginal communities, and Pentecostal churches are one of a few remaining social institutions surviving in this context. In the past ten years, gangs have transitioned from local criminal cliques to an influential social phenomenon. Pentecostals’ familiarity and access to gangs has many development practitioners looking to faith-based empowerment initiatives to solve broad social issues influencing gang expansion. At the same time, gang entanglement poses a distinct threat to the security and stability required to achieve sustainable development. As a practitioner of transformational development in El Salvador for over thirty years, I have recently observed the increasing isolation gang control is having on marginal communities. This article takes a closer look at the effects gang entanglement has on sustainable transformational development approaches in El Salvador, specifically examining three programs in the community of San Martín. The challenge is to identify transformational development policies, advocacy approaches, and support resources that best suit gang-entangled communities. To accomplish this, a larger discussion on transformational development in gang-entangled communities is critical.