This Article reviews the legal and environmental issues in bankruptcy matters involving: (1) a trustee responsible for dispersing funds to stakeholders, including those responsible for addressing environmental liabilities; or (2) alleged fraudulent transfer actions claiming inadequate environmental cost projections for environmental liabilities. In the first instance, the trustee must assign current costs for necessary and appropriate actions to achieve regulatory closure so that excess funds can be distributed to remaining stakeholders. In the second instance, a trier of fact considers the costs as of the date of the alleged fraudulent transfer to clean up environmental legacy sites. In both instances, stakeholders may have opposing views, those that contend cleanup costs are minimal and those projecting more costly actions. Common to both is the need to properly characterize the nature and extent of contamination, the risks posed to human health and the environment, and the associated environmental response actions needed. Ultimately, it is up to the trier of fact to weigh the legal issues, facts, and technical arguments to determine the necessary costs to address environmental legacy sites or portfolios.