This chapter provides an in-depth analysis of the persistent and intensifying challenges of flood risks in Matukeng, a peri-urban community in Lesotho’s Leribe district, situated within an ecologically sensitive floodplain. The study documents the spatial and temporal recurrence of localized flood events, particularly during the wet season between December and January, and their far-reaching socio-economic impacts, including structural damage to homes, disruption of livelihoods, public health crises, and infrastructural collapse. Drawing on historical records, local testimonies, and field-based observations, the chapter reveals how a convergence of hydrological vulnerability, poor infrastructure, and ill-conceived human settlement patterns has rendered Matukeng highly susceptible to flood-related disasters. Critically, the chapter interrogates the underlying causes of human settlement expansion in Eco-sensitive Zones (ESZs), focusing on the role of limited access to affordable land, informal peri-urban land markets, and hybrid land tenure systems that operate at the intersection of customary and statutory institutions. It highlights how fragmented governance structures and bureaucratic delays in the formal land registration process incentivize the occupation of flood-prone and environmentally sensitive lands. The emergence of “gray spaces”—settlements that exist between formal legality and informal legitimacy—reflects broader patterns of spatial injustice and planning failure in Lesotho’s peri-urban frontier. In response, the chapter proposes a set of environmental planning strategies and policy interventions tailored to ESZs in contexts of weak institutional enforcement and growing urban vulnerability. These include the adoption of integrated land use planning frameworks that incorporate flood risk data and ecological indicators; the promotion of green infrastructure solutions such as permeable pavements and rainwater gardens; the implementation of community-based conservation programs that engage residents in environmental stewardship; and regulatory reforms that align traditional and modern land administration systems. The chapter argues that addressing flood vulnerability requires more than technical fixes—it demands a fundamental rethinking of land governance, environmental justice, and urban resilience in Lesotho. Linking micro-level vulnerabilities to macro-level governance failures, the chapter contributes to a deeper understanding of how environmental planning, when embedded within inclusive and coordinated institutional arrangements, can offer sustainable solutions to the growing risks posed by climate variability and unplanned peri-urban expansion.