A methodology for optimized contaminated land investigation (OCLI) is described that balances the uncertainty of measurements against the cost of taking the measurements and the financial losses that may arise from misclassification of the land. Uncertainty from the sources of both field sampling and chemical analysis is estimated using existing techniques, based on the taking of duplicated samples. The actual costs of sampling and analysis and the expected costs that could arise from either 'false positive' or 'false negative' classification of areas of land were estimated. A loss function was constructed that calculates the expectation of financial loss that will arise for a given uncertainty of measurement. The function shows a clear minimum value of cost at an optimal value of uncertainty. Application of this OCLI technique to two case studies demonstrated this minimum value. Below the optimum value of uncertainty, the costs increased due to higher measurement costs. Above the optimum, the costs increased due to increasing risk of factors such as unnecessary remediation or potential litigation over undetected contamination. Many areas for further development of OCLI are identified, but the technique is demonstrated as a useful new approach to judging fitness-for-purpose of such measurements.