Driven by internationalization efforts such as those that accompanied the global efforts to combat the illicit drug trade, international law enforcement efforts by the United States have developed markedly over the past few decades. A notable element of this phenomenon has been the increased need by domestic law enforcement agencies to conduct extraterritorial law enforcement operations. This is especially so in "ungoverned spaces" -- areas of the world where there is no governmental counterpart willing or able to take action. The U.S. response to transnational crime has, however, frequently taken on the characteristics of military action -- a trend that has worried policy makers and senior military officials. A resort to military assets can be practical on multiple levels. But aside from the myriad practicalities which ordinarily compel national leaders to resort to the most capable organ of state power when difficult situations arise, there are also compelling international legal considerations that make the use of military force an even more tempting option when dealing with the unique challenges posed by transnational criminals operating outside the United States. In fact, as this Article demonstrates, the use of military force may frequently be the only option legally permissible under the current state of international law. This stems from a dramatic dichotomy in international law that tightly constrains the range of conduct permitted during extraterritorial civilian law enforcement operations while granting the military (in certain circumstances) wide latitude to carry out an almost unlimited range of invasive and even lethal activity. This Article explicates the international legal rules governing the exercise of extraterritorial enforcement jurisdiction by civilian law enforcement agents. In so doing, the Article reviews the various legal bases under which civilian law enforcement agents may operate abroad, including treaty-based authorities such as the historic capitulatory regime, more modern Status of Forces Agreements (SOFAs), and various operations undertaken pursuant to the consent of the host nation. The Article contrasts the limits placed on extraterritorial activity by law enforcement agents to the more extensive activities permitted to military actors under the Law of Armed Conflict (LOAC). The article also notes capabilities and limitations of various domestic legal structures, drawing on examples of law currently in place in the United States, Tunisia, and Libya. The Article posits that the international legal strictures on unilateral law enforcement activity are, in part, responsible for the militarized approaches to transnational crime which have become a cause of concern for both senior military leaders and human rights advocates. Accordingly the Article advocates for greater latitude under international law. To that end, the trend of militarization in the U.S. approach to transnational crime could be reversed to a degree if international law recognized a greater degree of flexibility for certain limited categories of extraterritorial law enforcement actions by civilian actors. It is argued that permitting such an exception would simultaneously promote 1) policies of refocusing the military on war-fighting by limiting its role in combating transnational crime and 2) rights-based approaches and government transparency by addressing transnational criminality in a way that comports with constitutional due process and international human rights norms.