Targeted sanctions are often judged by whether they compel behavioural change among political elites, yet their effectiveness is uneven across conflict settings. In South Sudan, sanctions frequently fail not because elites are inherently resilient, but because coercive measures are mismatched to the informal and transnational financial networks through which power is exercised. The concept of adaptive sanctions evasion captures how sanctioned actors adjust by rerouting assets, mobility, and commercial access through regional and offshore infrastructures. Situated within debates on sanctions effectiveness, compliance and evasion, and the political economy of constraint, the manuscript examines how design interacts with evasion capacity in conflict economies. Focusing on South Sudan, with comparative reference to Zimbabwe and the Democratic Republic of the Congo, the study addresses three interrelated questions: how targeted sanctions regimes (UN Security Council measures and U.S. Executive Orders) shape the financial and mobility calculations of designated individuals, and through which mechanisms compliance or evasion occurs; how different design features—such as asset freezes, travel bans, and arms embargoes, as well as unilateral versus multilateral approaches—affect elite incentives; and how regional evasion infrastructures, particularly through the United Arab Emirates, Uganda, and Kenya, enable sanctioned actors to maintain access to financial systems despite formal restrictions. Methodologically, the study combines structured analysis of UN Security Council and U.S. Treasury OFAC designations, financial intelligence and asset recovery case analysis, expert interviews with UN Panel of Experts members, U.S. Treasury officials, and South Sudanese private sector actor