Iran and Venezuela, two nations under heavy Western sanctions, have sought to build strategic partnerships over the past two decades. Their alliance has been framed as a counterbalance to U.S. hegemony, rooted in shared ideological narratives and economic needs, particularly in the oil and energy sectors. However, despite grand rhetoric and high-level agreements, the relationship has often yielded limited tangible results. Recent developments suggest that Iran may be facing setbacks — or even failures — in its engagement with Venezuela, with significant political, economic, and geopolitical consequences.