At first sight, relations between politics and the military in Macedonia, one of the ex-Yugoslav republics that gained independence in 1991, seem to resemble the typical evolution of civil–military relations in other countries in transition. Yet, history in Macedonia is far from straightforward and simple. First, the country’s appearance on the world scene was unique: it was practically a demilitarized state with no army! Apart from that, amid the Yugoslav imbroglio it was known as an “oasis of peace.” Only 10 years later, in 2001, Macedonia found itself on the verge of an ethnic conflict, with a powerless (Macedonian-dominated) military that confronted apparently well-organized Albanian paramilitary forces. In March 2020, Macedonia became NATO’s 30th member state. Yet, the dilemma that affects civil–military relations at both the political-military and societal-military levels has not gone away. Theoretically and practically, any meaningful analysis requires detection of the troublesome aspects of each side of the triangle: state/politics/military/society/ethnicity. Though the society–state dimension is far from inconsiderable, on methodological grounds the analysis that follows is restricted to the other two dimensions. NATO membership for a transitional country usually presupposes a successful democratic transition, internal stability, and societal consensus over key national values and interests. Macedonia’s case belies that assumption. The Macedonian military has been practically invisible in internal politics, while it has been widely cited as a key asset for bringing the country closer to NATO by direct involvement in military interventions launched by the United States or NATO, starting with Afghanistan and Iraq and extending to the plans for involvement in Mali’s affairs. Behind the façade, there is silent internal strife within the ranks along political and ethnic lines (i.e., the same lines that sharply divide the state and society, challenging the country’s internal cohesion and democratic prospects). In addition, the military has to make do with scant essential resources, while the military officers’ self-respect is severely diminished by the low societal rewards for their profession. Macedonia’s democratic transition is far from complete, since the country is going through a deep internal crisis related to its societal/security dilemma, and the military is just one of the institutions that suffer because of ethnic competition and unprincipled power-sharing bargaining.