The law and practice concerning the responsibilities of businesses and the obligations of their home states in relation to private dealings in occupied territory are under-developed. The establishment of a database by the United Nations (UN) Office of the High Commissioner for Human Rights to monitor the activities of corporate actors in the Occupied Palestinian Territory (OPT) is an opportunity to provide much-needed guidance on the scope of application of existing international law in this paradigmatic case of a high-risk business environment. This article engages with the contribution of this initiative to the regulation of transnational corporate dealings through two normative issues: the structural characteristics and effects of the violations taking place in certain business environments maintained in the OPT on the responsibilities of business and home states; and the various modes through which businesses become directly linked with and contribute to the illicit property rights regime underpinning the existence of settlements and the serious human rights abuses perpetuated by their maintenance.