Driven by more intense rainfall, expansion of impervious surfaces, and aging drainage infrastructure, flash flooding in urban areas is becoming increasingly commonplace across the United States.  Providing flood relief in fully developed areas is expensive and almost always subject to space constraints. Using the 2D modeling capabilities of software such as XPSWMM can reveal complexities of existing drainage infrastructure and overland flow that may otherwise be missed when using more simplistic modeling approaches.  This presentation will showcase recent examples where 2D hydraulic modeling provided insights that allowed GKY to recommend design solutions that provide effective flood relief and work within the constraints of urban sites.