In this paper, we utilize the public Bitcoin blockchain to track and monitor the movement of Bitcoin from official government sanctioned entities. Specifically, we examine the flow of Bitcoin to and from sanctioned addresses to exchanges and identify the impact that regulations have on those flows. We find that regulations cause a significant decline (increase) in inflows (outflows) to exchanges, suggesting that regulations do have the desired effect. However, we show that the quality of the legal system is a significant, in that the regulation needs to passed in the country of the exchange to have the desired effect. Therefore our analysis shows that regulators wanting to limit the usage of exchanges in their countries by sanctioned entities should regulate the exchanges and have a high level of regulatory quality. Additionally, the paper scrutinizes the influence of countries' legal system quality and socio-cultural factors on the effectiveness of regulatory interventions. By considering the interplay between regulatory frameworks and societal dynamics, it provides valuable insights into the varying efficacy of regulations across different contexts. Ultimately, this study underscores the complexity of regulating Bitcoin flows from sanctioned entities and ransomware attackers, emphasizing the importance of tailored regulatory approaches informed by both technical and sociopolitical considerations.