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The passage in the U.S. Congress of HR 49391 in late 2016 was a significant development. It has had the potential of focusing U.S. policymakers’ attention on a region most often deemed of secondary interest, or parceled out in small, generally disjointed policy fragments. But it easily also invites skepticism that the passage of legislation is in no way confirmation of a serious long-term commitment to the Caribbean by Washington. And then there is a counterpart Caribbean reality that also must be factored in, and the prospects that the way the region defines its own interests can influence, let alone shape, U.S. policy. Even when acting from a joint or integrated Caribbean perspective, there is the potential for a mismatch in the scale and scope of perceived strategic hazards—what may be articulated as an existential threat in the Caribbean does not always measure in parallel terms with U.S. policymakers. Nevertheless, HR 4939 provides a once-in-a-generation opportunity to address these realities and trigger a robust Caribbean policy dialogue that addresses core interests. This requires some serious work.