In watersheds across the U.S., there are utility poles and other critical infrastructure that are vulnerable to flooding damage. The goal of this multidisciplinary research is to assess and minimize the probability of utility pole failure through conventional hydrological, hydrostatic, and geotechnical calculations embedded to a mixed-integer linear programming (MILP) optimization framework. Once the flow rates that cause utility pole overturn are determined, the most cost-efficient subterranean pipe network configuration can be created that will allow for flood waters to be redirected from vulnerable infrastructure elements. The optimization framework was simulated using the Julia scientific programming language, for which the JuMP interface and Gurobi solver package were employed to solve a minimum cost network flow objective function given the numerous decision variables and constraints across the network. We implemented our optimization framework in three different watersheds across the U.S. These watersheds are located near Whittier, NC; Leadville, CO; and London, AR. The implementation of a minimum cost network flow optimization model within these watersheds produced results demonstrating that the necessary amount of flood waters could be conveyed away from utility poles to prevent failure by flooding.