Dioxins are environmental pollutants, potentially present in milk products, which have negative consequences for human health and for the firms and farms involved in the dairy chain. Dioxin monitoring in feed and food has been implemented to detect their presence and estimate their levels in food chains. However, the costs and effectiveness of such programs have not been evaluated. In this study, the costs and effectiveness of bulk milk dioxin monitoring in milk trucks were estimated to optimize the sampling and pooling monitoring strategies aimed at detecting at least 1 contaminated dairy farm out of 20,000 at a target dioxin concentration level. Incidents of different proportions, in terms of the number of contaminated farms, and concentrations were simulated. A combined testing strategy, consisting of screening and confirmatory methods, was assumed as well as testing of pooled samples. Two optimization models were built using linear programming. The first model aimed to minimize monitoring costs subject to a minimum required effectiveness of finding an incident, whereas the second model aimed to maximize the effectiveness for a given monitoring budget. Our results show that a high level of effectiveness is possible, but at high costs. Given specific assumptions, monitoring with 95% effectiveness to detect an incident of 1 contaminated farm at a dioxin concentration of 2 pg of toxic equivalents/g of fat [European Commission's (EC) action level] costs €2.6 million per month. At the same level of effectiveness, a 73% cost reduction is possible when aiming to detect an incident where 2 farms are contaminated at a dioxin concentration of 3 pg of toxic equivalents/g of fat (EC maximum level). With a fixed budget of €40,000 per month, the probability of detecting an incident with a single contaminated farm at a dioxin concentration equal to the EC action level is 4.4%. This probability almost doubled (8.0%) when aiming to detect the same incident but with a dioxin concentration equal to the EC maximum level. This study shows that the effectiveness of finding an incident depends not only on the ratio at which, for testing, collected truck samples are mixed into a pooled sample (aiming at detecting certain concentration), but also the number of collected truck samples. In conclusion, the optimal cost-effective monitoring depends on the number of contaminated farms and the concentration aimed at detection. The models and study results offer quantitative support to risk managers of food industries and food safety authorities.