Despite the ongoing sanctions regime, many foreign companies continue their operations in Crimea without any legal repercussions. The purpose of this article is to highlight the common patterns of sanctions circumvention used by Western firms in order to keep their businesses in Crimea. By juxtaposing the companies’ justifications and their behavior, this article assesses the companies’ activities vis-à-vis the sanctions’ legal framework. The article reveals the weaknesses within the sanctions regime and makes policy recommendations for the enhancement of the effectiveness of sanctions.