Polychlorinated biphenyls (PCBs) are persistent organic pollutants banned under the Stockholm Convention but still detected in contaminated soils, biota, and food matrices after production stopped. In northern Italy, the Caffaro chemical plant in Brescia, operated as one of Europe's largest PCB manufacturers until the 1980s and, now designated as a Site of National Interest (SIN) for this contamination. The distribution and the concentration of parent PCB congeners in this region have been documented but less attention has been given to their transformation products including sulfonated PCBs (PCB-SO3H), hydroxylated-sulfonated PCBs (OH-PCB-SO3H), and hydroxylated PCBs (OH-PCBs). These metabolites are product during biotic and abiotic degradation and can have different environmental mobility, bioaccumulation and toxicity profiles that are still unknown.  Recent investigations revealed PCB-SO₃H and OH-PCB-SO₃H as novel categories of intermediates of PCB degradation in soil, accounting for about 1% of parent compounds. These metabolites tend to bioaccumulate in earthworms although their ecotoxicity is still unknown. Additionally, their behavior in the soil-plant ecosystems and the possibility of their entry into food chains have not been adequately elucidated. This study investigated PCB and PCB metabolite levels in soils, plant biomass, and other media collected around a historical PCB landfill in Passirano (Brescia province), where industrial waste from Caffaro and other industrial plants was stored in a landfill. The main aim was to assess whether this localized contamination source could generate measurable concentration gradients across the surrounding environment and to evaluate possible transfer pathways from soil to vegetation. The results contribute to a better understanding of PCB cycling in legacy-contaminated agricultural soils and underline the need to include metabolite monitoring alongside parent congeners in environmental risk assessments.