The present article is dedicated to comprehensive analysis of business-risks in Syria in the security sphere (the author named it as “security trap”). Among them are the seats of combat activities between the government forces and the opposition, contradictions between the central government and local elite, rise in criminality among former combatants, traumatized by war, “urban” terrorism, stepped up activity on the part of ISIS militants in desert areas and not in the last measure the conflicts of interests among external actors. This topic seems to be quite new for scientific research in Russia and abroad since most analytical work has been previously focused on impacts of security in military political and social spheres rather than in the economic one. Such approach would allow us to make a conclusion that business risks alongside other difficulties such as territorial fragmentation, economy lying in ruins, sanctions, crisis in neighboring Lebanon, COVID-19 pandemic are hampering the revival of businesslike life. This is important and useful for constructing hierarchy of external and internal challenges for Syria’s post-conflict reconstruction, including the stabilizing role of Russia. The author has used empirical materials gathered during the term of his diplomatic service at the Russian Embassy in Damascus (in 2014–2017) along with his subsequent regular visits to Syria.