The aim of this paper is to review NATO's Defence Education Enhancement Programme (DEEP) and to bring to the fore the measures of effectiveness regarding its implementation and to determine its shortcomings in the South Caucasus region. At the same time, the paper highlights the efforts of the DEEP teams to influence the partner educators through dialogue and encouragement. The authors refer to the best examples considering the measures of effectiveness. Considering the outcomes achieved by the partner nations, they endeavoured to apply Kirkpatrick model for measuring DEEP's effectiveness in the South Caucasus countries. The paper discusses how they can more effectively address the challenges in their professional military education (PME) through their tailored DEEPs. The paper analyzes the processes that led by the South Caucasus nations, their national interests and what steps still need to be taken to realize their ambitions to be intellectually interoperable with NATO forces.