This article explores the complexities surrounding dividend withholding tax reclaim processes and their impact on foreign direct investment returns. It first highlights the growing trend of investors seeking opportunities outside their local stock exchanges and investing in shares abroad or dual-listed shares. Through advanced technology, cross-border transactions have become more prevalent, allowing resident investors to easily purchase shares in foreign markets and non-resident investors to invest in local markets.The refund process often involves submitting extensive documentation, lengthy processing times, potential time limitations for claiming refunds, burdensome administrative procedures, language barriers in foreign jurisdictions, unfamiliar legal requirements, and the possibility of audits or reviews by tax authorities to validate refund claims. Examining these complexities and their impact, this article employs a doctrinal research approach comparing different treaty practices across the Southern African Development Community, also in relation to third countries. It reveals that the complexities of dividend withholding tax reclaim processes significantly affect foreign direct investors’ returns on investment. The article emphasizes the importance of enhancing transparency and consistency in these processes, streamlining documentation requirements, and developing efficient electronic systems.