This paper examines the phenomenon of artificial profit shifting as a component of illicit financial flows. Uganda’s upstream oil sector involves a rent sharing regime with the non-resident international oil companies. The involvement of international oil companies creates taxing rights for host governments. Unfortunately, these rights can be susceptible to artificial profit shifting - an aggressive strategy of tax avoidance which contravenes applicable anti-abuse tax laws and therefore falls within the prescriptive envelope of illegality. This paper discusses the unique opportunity for the application of anti-abuse tax laws and the need for judicial cooperation in doing so, as a tool against artificial profit shifting; whose negative impact on the tax-to-GDP ratio continues to undermine Uganda’s efforts in domestic resource mobilisation to alleviate poverty.