A historical commercial and migrant intersection, Yemen’s strategic location at the mouth of the Red Sea and crossroad of three continents have contributed greatly to regional and international interest in Yemen’s internal security. Renewed regional and international geopolitical competition, continued efforts to combat the threat of international terrorism and Islamic extremism emanating from the region, and changes to the flow of oil resources due to other regional security concerns have only increased Yemen’s strategic importance to the global economy and a priority in the national security agendas of regional and international actors alike. Such considerations have not been lost on Yemen’s domestic incumbent and insurgent political, tribal and military elites, contributing, in part, to domestic political and military strategies meant to perpetuate a perception of internal insecurity that threaten the strategic interests of external regional and international stakeholders. The paper examines Huthi expansionism in the broader context of a domestic elite strategic culture that promotes perpetual insecurity and internal war, and namely how strategic considerations of regional and international actors influence the policies and actions of Yemen’s domestic elites, both incumbents (elites within the system) and insurgents (elites excluded from or opposed to the system), through comparison of three periods of the internal war in the Yemen (1994, 2004-2011, 2015-present). The history of internal war in Yemen has shown that conflict creates unlikely alliances and strange bedfellows, and the current conflict is no different, owing to a strategic logic of perpetuating conflict and creating/exacerbating divisions in an effort to consolidate/seize power. The paper utilizes theoretical and comparative approaches as a tool for analyzing the strategic factors and decision making that have contributed to perpetual insecurity punctuated by periods internal war in Yemen, with a particular emphasis in understanding the strategic dynamics driving Huthi expansionism and domestic, regional and international responses to it.