Managed retreat has become a recommended adaptation strategy for hazard-prone coastal cities. The study aimed to improve considerations for the contextual factors that influence the success of managed retreat and resettlement projects in Metro Manila. Data were collected through a mixed-method approach consisting of a screening of relevant literature, a qualitative case analysis of resettlement projects, and a workshop series with Philippine stakeholders. It turned out that the resettlement of informal settlers is a central element of urban development. Though in-city resettlement is preferred, most existing and planned projects are developed in off-city locations. The findings present a nuanced view of different retreat approaches. Not all in-city resettlements are successful, and unpopular off-city projects are potentially important for urban and regional development. A strategic planning thread to develop concepts for qualitative off-city settlements that counteract uncontrolled urban sprawl with monofunctional residential areas for urban poor people was deduced. The other thread asks for pathways for inner-city development with innovative, vertical, in-city projects. A final observation was that climate change and the COVID-19 pandemic are worsening the situation in informal settlements, thus strengthening the argument for the planned decentralization of Metro Manila's congested urban areas.