When a state joins two regional organizations (ROs) pursuing such different objectives in the same region as integration and security, international relations scholarship focuses on whether the obligations defined by the one organization are compatible with those laid down in the other. On the other hand, when a state belongs to two ROs with the same policy scope but in different regions, the possibility that this “regional overlap” creates conflicts between differing normative and institutional commitments that can generate contradictions rather than complementarities for the government involved is considerably more challenging for analysts. These dilemmas were raised in 2012 by Mexico when, already a member of the North American Free Trade Agreement since 1994, it founded the Pacific Alliance with three far-off countries, Chile, Colombia, and Peru. This paper tackles four puzzles that the resulting regional overlap presented: Why, when its trade was overwhelmingly directed at the North American market, did Mexico join the Pacific Alliance offering poor prospects for increasing its foreign commerce? How, as a third world rule-taker on trade issues, did it become a first world rule-maker which urged the new Alliance to adopt NAFTA’s foreign direct investment protection norms and institutions? In border security matters, was Mexico finding allies who could help the country resist overbearing US demands for collaboration in its “wars” on drugs and terrorism or was it diffusing Washington’s norms southwards to its fellow member states in the Andes? Were the geopolitical implications of Mexico’s regional overlap to reaffirm its credentials in Latin America or to support the United States’ efforts to offset the consolidation there of China’s trade, investment, and security presence? Our discussion of these four puzzles will reveal a surprising set of complementarities rather than contradictions between Mexico’s policy obligations, actions, and prospects in these two distinct ROs.