Purpose: This study delves into the relationship between jurisdictional divergence and the enforcement of punitive measures for cross-border intellectual property (IP) violations. It aims to explore how varying legal frameworks, procedural differences, and cultural influences within jurisdictions impact the severity and imposition of punitive actions in cross-border IP contexts. Method: Utilizing a qualitative approach, this research conducted 15 in-depth semi-structured interviews involving knowledgeable stakeholders in cross-border IP enforcement. Thematic analysis of qualitative data followed a three-stage process, aiming to reveal nuanced connections between jurisdictional divergence and punitive measures' imposition. The method ensured a comprehensive exploration of themes related to this intricate subject. Findings: The study uncovered critical insights into the influence of jurisdictional divergence on cross-border IP enforcement's punitive aspects. Key discoveries emphasized the significant impact of conflicting legal systems, procedural disparities, and cultural perceptions on the consistency and severity of punitive actions. Additionally, it revealed a direct link between the severity of IP violations and the magnitude of imposed punitive damages, highlighting the pivotal role of violation impact in enforcement decisions. Implications/Originality: The research contributes theoretically by addressing gaps in understanding how jurisdictional disparities intricately shape punitive measures in cross-border IP enforcement. It also provides practical insights guiding policymakers, legal practitioners, and rights holders in navigating this complex landscape, emphasizing the need for standardized approaches to address jurisdictional challenges in cross-border IP enforcement.