The history of Russia's relations with Israel goes back as far as the founding of this country. While the Kremlin has always attached great importance to Tel-Aviv, Russia-Israelrelations have gone through various tests in some periods. One of these processes is undoubtedly the Syrian civil war. In 2011, the Arab uprisings that started in the Middle East turned into a civil war in Syria, which became more complicated and created a new threshold for the region. Seeing its interests in Syria in parallel with the Assad regime, Moscow directly intervened in the civil war in 2015 and chose to support the regime. The relations between Russia and Israel, which took opposing sides in the civil war, brought along the perception of mutual threat. However, the continuation of commercial ties between the two countries during this period brought along an interesting dilemma. Even though the two countries directly confronted each other with the "airplane crisis" during the Syrian civil war, this crisis was overcome in a short time. Paradoxically, Russia's maintenance of both levels of relations in the Syrian civil war is a product of Moscow's traditional pragmatist approach. The aim of this study is to reveal the reasons for Russia's perception of Israel as a security threat during the Syrian civil war while maintaining trade with the country. It also focuses on the variables through which and how this contradictory relationship is realized. The study also uses discourse analysis, in addition to content analysis, one of the scientific research methods. As a result of the analysis, the reasons for Russia's dilemma in its relations with Israel in the Syrian Civil War are presented in a reasoned manner.