The emergence of the Armenian Revolutionary Federation (A.R.F.- also known as the Dashnaks) in 1890, marked the opening of a new front of guerrilla warfare initiated by the ethnic minorities of the Ottoman Empire throughout the second half of the 19th century. A scrutiny of Dashnak activities from the 1890’s until the early 1900’s, indicates a gradual improvement of military strategies and operational tactics. This paper argues that the establishment of the Dashnak military academy in Bulgaria in 1906 was a crucial element in the institutionalization of the A.R.F. military platform, which was dictated by the political and military developments of the region at the time. In other words, this paper attempts to understand the history of the academy, by putting it in the context of Armenian-Bulgarian/Macedonian cooperation on the one hand, and the expansion of the Dashnak operational terrain in the Balkans as well as the Caucasus stipulated by A.R.F. Congresses on the other. Given the scarcity of the material on this particular topic, I will utilize published A.R.F. and Ottoman archives as well as secondary literature, in order to gauge the political/military implications of this academy and its significance in generating cross-fertilization among revolutionary organizations in the Ottoman Empire in the early 20th century.