The paper describes the Polish road to NATO which, contrary to the West’s expectations and promises, was long and bumpy. The author presents and analyses various obstacles that hindered Polish accession to NATO. The author divides such challenges into objective and subjective barriers, but using other criteria, the author points to specific geopolitical, international, political, social, and military conditions. Furthermore, the author presents the stances of different countries on the enlargement of the North Atlantic Alliance after the Cold War, particularly the attitudes of the USA, Germany, France, the USSR, and Russia as these states were either more or less supportive of Polish efforts to join NATO or not supportive at all. In 1989-1999 the Alliance’s position was slowly evolving from being initially unwilling to support Poland’s accession to NATO to being sympathetic towards it. In the paper, the author poses a few research questions on the above-mentioned obstacles on the Polish road to NATO and a few theses and hypotheses. The author states that primarily the USSR, later the Russian Federation, was against Poland’s accession to NATO. Initially, the West also opposed it. After 1989, its priority was to reunite Germany and stabilize military relations with Moscow through the Treaty on Conventional Armed Forces in Europe (CFE) and the elimination of Soviet military bases in post-communist countries of Central and Eastern Europe.