Urbanization has been linked to destructive geo-hazards that can cause loss of life, destruction of property, and environmental damage. On August 14, 2017, a devastating geo-hazard chain—a debris slide, debris flow, and sediment-laden flood—in Freetown, Sierra Leone resulted in at least 500 deaths and over 600 missing persons and the destruction of hundreds of houses. This study uses 10 years of high-resolution satellite images to conduct a remote sensing analysis of the disaster. Although rainfall was the trigger, rapid and haphazard urbanization acted to increase both hazard and vulnerability. Specifically, poor urban planning with inadequate consideration of risk led to housing construction in dangerous areas; clearance of hillside vegetation increased erosion potential; very low cost buildings using frail construction material and methods lacked resilience; and insufficient risk management led to weak emergency response.