In this paper, I focus on the activities of Shan traders on the Myanmar-Thai border, especially on their interaction with state authorities, which can result in proactive and reactive practices triggered by regulations on the trading of particular commodities. To date, most of the studies on cross-border trade have mainly centred on merchants’ strategies in response to border regulations imposed by the state (Konstantinov, 1996; Walker, 1999; Wallace, 1999; Kusakabe, 2004; Williams & Baláž, 2005; Turner, 2010; Harris, 2013; Endres, 2014). My goal is to elaborate trade strategies from the aspect of commodities’ meanings given by traders and state actors. When transporting goods into Thailand, traders are known to manipulate the intricacies of regulations by diverting commodities’ meanings to suit their business aims. Meanwhile, mundane practices of state actors are conducted within a ‘regulatory space’ (Abraham & van Schendel, 2005) in which dominant and alternative construction of meanings often are in contestation. I argue that everyday cross-border transactions coexist with the interaction between the implementation and performance of state authority and traders’ proactive and reactive responses. As a result, some forms of exchange can confound the boundary between gifting and bribery. Depending on the giver’s desired manners (Smart, 1993), gifting practices are associated with other types of social behaviour (Sherry Jr., 1983, p. 158) and can possibly be interpreted as distinct from bribery. Consequently, the subtle crossover from gift to bribe can result in a negotiable space where illegal actions are accepted as licit.