The aim of this study was to develop a toolset that can be used by site managers to assess and monitor natural attenuation processes in sediments contaminated with legacy hydrophobic organic contaminants. The toolset is composed of sediment traps to measure quality and deposition rate of incoming sediment under different hydrodynamic conditions, sediment cores to show trends in sediment bed concentrations over time, and passive samplers attached to a porewater probe frame to assess the mobility of buried contaminants and possible contaminant flux from sediment. These three tools were used together for the first time to assess the mobility of dichlorodiphenyltrichloroethane (DDT) contaminants in sediment in Pallanza Bay, Lake Maggiore, Italy. Depositing sediment and sediment cores were consistent in showing that DDT-contaminated sediment is undergoing burial by cleaner sediment. Elevated DDT concentrations from historical contamination seemed to be effectively buried and immobilized by ongoing deposition by cleaner sediment, because the positive flux from the elevated DDT concentration in the sediment porewater should not advance towards the sediment surface. The monitoring toolset introduced in this study enabled us to more effectively assess ongoing natural attenuation processes and provide more risk relevant data than traditional methods used in monitored natural recovery projects, such as bulk sediment concentrations from sediment cores. Our field assessment results suggest that incoming sediment from the Toce River have reduced DDT concentrations in the sediment compared to historic levels, and will continue to do so in locations where higher DDT concentrations are found within the bioactive layer.