Karst aquifers are very vulnerable to various pollution sources. Among these, landfills can contribute contaminants over long periods. Groundwater quality monitoring is required to assess the impact of a landfill leachate on underlying aquifer water or spring discharge. Tracer tests are useful for selecting the location and frequency of sampling. Three landfill sites in karst areas were studied with tracer tests. Additional insight was accomplished by the comparison of the tracer transfer and the breakthrough curves obtained from these tests with the results of two other tracer tests carried out in the same period in karst areas without a landfill. To explain the differences observed, the hypothesis of increased permeability below the landfill due to the presence of inorganic acids in leachates was further tested. The results of detailed, long-term monitoring of contaminated drip water in the Postojna Cave were used to verify the hypothesis. The analysis of the simultaneously increased content of calcium, magnesium, and contaminants in the drip water indicates a direct correlation between limestone dissolution and contaminants. Increased dissolution increases secondary porosity and thus permeability of the vadose zone resulting in higher vulnerability of underlying aquifers and springs in the vicinity landfills.