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This study reevaluates the concept of "smuggling," extending beyond its common portrayal in the media as an underground and organized criminal activity. Conducted within the Southern Chinese Seaboard, a region marked by diverse taxation and legal jurisdictions, our research applies institutional and discourse analysis to investigate the legitimation and criminalization of cross-border trade between Taiwan and China, and between the Hong Kong SAR and mainland PR China, amidst rapidly evolving political-economic and regional geopolitical dynamics. We challenge the simplistic perception of illicit and parallel trading as merely spontaneous actions by individuals embedded in criminal networks. Instead, we posit that such activities stem from deliberately vague legal definitions and enforcement strategies, resulting from the collusion between state and non-state actors. Utilizing the "Regime of Permission" framework, we delve into how political actors manipulate the definitions of licit and illicit trading to achieve political objectives, thereby unintentionally creating loopholes that non-state actors exploit. Our findings provide deeper insights into the state's role in regulating lawful and unlawful trade activities, demonstrating how the delineation of illicit trade and its oversight have evolved in response to changing economic relationships and the development of enforcement institutions within the region's shifting geopolitical landscape.