This study analyzes the Democratic People’s Republic of Korea’s (DPRK—or North Korea) economic exchanges with Russia and the European Union (EU) from an institutional perspective. Trade statistics show that between 2000 and 2012, the DPRK conducted more trade with the EU than with Russia, its neighbor and former socialist ally. This observation provokes the following questions: In what way does the institutional environment in Russia and the EU impact on economic exchanges with the DPRK? Why have Russia’s economic exchanges with the DPRK remained limited despite a common land border? Of particular interest is the cooperation between the Russian Far East (RFE) and North Korea. What does the institutional set-up in the RFE imply for business opportunities in North Korea? To examine the so far little researched role of the RFE, this study uses quantitative and qualitative data provided by the Russian Federal Customs Service and the district governments of Khabarovsk and Primorye. The findings show that political, legal, and normative factors as well as different business practices impact on economic exchanges with the DPRK in various ways.