This article investigates the relationship between international entrepreneurial orientation (IEO) and international performance taking into account the moderating effects of politicization in internationalization decisions and international hostility. Using data from 208 Greek international small and medium-sized enterprises (SMEs), we found that IEO is positively related to international performance. We also found that neither politicization nor international hostility separately has any moderating effects on this relationship. However, the findings support the view that the combination of high levels of politicization and international hostility critically diminishes the effects of IEO on international performance. These findings enrich the international entrepreneurship field that has been relatively devoid of investigations examining decision-specific aspects of the firm.