The Shiprider Agreement — an important aspect of Jamaica-US bilateral diplomacy — represents the strength of diplomatic engagements that have been used to address the cross-border drug-trafficking problem. To substantiate this claim, this article examines the Jamaica-US Shiprider Agreement on three criteria.First, examining some examples of counter-drug cooperation before the Shiprider Agreement demonstrates that the fundamental basis for the Agreement is premised on a positive Jamaica-US relationship. This relationship, along with the stipulated obligations enshrined in the 1988 Vienna Convention, impelled the United States' proposal of the Shiprider Agreement. Second, the article uses complex interdependence theory to test the negotiation process and the outcome of the Agreement. Findings demonstrate that complex interdependence mainly confirms explanations of the foreign policy outcomes and diplomatic conduct displayed in the Jamaica-US Shiprider case. Finally, the article assesses the breakdown in the negotiation process and the initial implementation phase of the Agreement, arguing that this breakdown must be seen in context given the Agreement's successful ratification and its non-controversial continuation. The article concludes that despite the instances of breakdown, the birth and provision of the judicious Jamaica-US Shiprider Agreement owed much to the success of diplomacy.