In international trade, there are a number of aspects that influence the interactive relationships between business organizations and governmental organizations, which makes it difficult to regulate the business processes in an integrated way. Modeling such kinds of organizational interactions requires a mechanism to differentiate interactive environments and elaborate regulations according to their characteristics. For this purpose, a context-aware inter-organizational modeling approach is proposed in this paper. The approach analyzes organizational interactions through three phases from abstract to concrete: (1) general specifications which describe organizations in terms of atomic roles with intellectual objectives, (2) contextual specifications which extend general specifications by applying contexts to derive composite roles with details on how to accomplish the objectives, and (3) operational specifications which construct a set of complete models of an inter-organizational collaboration by assembling contextual specifications according to the run-time environment. An example consisting of two scenarios of direct control and self-regulation in international trade is used to illustrate our model.