Although they were never confirmed conquerors, the total waiver for loss and damage caused by the Japanese in the Pacific war under Article 14(b) of the Treaty of San Francisco conferred a blanket sovereign immunity on them in the jurisdictions they invaded including the Philippines, Malaya, Singapore and Hong Kong. As occupiers under the Convention (IV) respecting the Laws and Customs of War (the Hague Regulations) the evaluation of Japanese state practice and liability to pay compensation arising from misuse of civilian-owned private property rests entirely on the validity of Article 14(b). This paper takes the prospects of the Hong Kong Chinese of winning individual-to-state reparations as an example of how a new reparations model could work. In particular, it surveys financial losses that were incurred by them during the Japanese Occupation (1941–1945). The misapplied sovereign immunity granted to the Japanese for wartime loss and damage under Article 14(b) has allowed them to escape evaluation as occupiers. But recognizing Article 14(b) as void would not necessarily open the flood gates if the moderating elements of military necessity and an occupant’s monetary policy prerogative were applied. Thus, rather than focus on the loss of value of money through confiscatory currency exchange rates, rampant price inflation or demonetization, a new reparations claim should focus on money taken by the Japanese of non-Kwomintang Hong Kong Chinese in house-to-house requisition drives and from bank deposit accounts.