The increasing incidence of extreme precipitation events, compounded by urban and suburban expansion, has led to elevated runoff rates and catastrophic consequences at historically constrained stream cross-sections, such as road crossings featuring culverts. Rising water levels and swift bypassing currents pose imminent threats to vehicular and pedestrian safety, often resulting in property loss and fatalities. An under-explored contributing factor to this heightened risk is the accumulation of woody debris, particularly during storm events. This presentation aims to shed light on this issue through field evidence collected following Hurricane Ida in New Jersey in 2021 and a significant rainfall event in Pennsylvania in 2023. In addition, a comprehensive review of existing literature will be presented, focusing on the dynamics of woody debris generation, transport, and jamming, as well as their ensuing impact on rapid water level rises and accelerated stream flow. The presentation will conclude by identifying research gaps and outlining broader societal impacts, including recommendations for woody debris monitoring, flash flood forecasting and alert systems, and strategies for enhancing infrastructure and community resilience, as well as effective management of wooded and riparian zones.