This chapter traces the historical trajectory of Bulgaria’s economic development and foreign economic relations from its postliberation period in 1878 through the socialist era to the transition to a market economy. It argues that Bulgaria’s economic evolution has been marked by a persistent reliance on dominant external partners—Germany, the Soviet Union, and later the European Union—which has often led to structural inefficiencies and economic vulnerabilities. The chapter is structured into three key sections: the first examines Bulgaria’s early attempts at industrialization and its growing dependence on Germany before WWII; the second analyzes the socialist period, highlighting Bulgaria’s integration into the Soviet-led COMECON, rapid industrialization, and subsequent economic challenges; and the third explores the tumultuous post-1989 transition characterized by rapid liberalization, deindustrialization, and socioeconomic upheaval. Through a critical historical lens, the chapter underscores the risks associated with both economic isolation and premature liberalization without adequate institutional preparation. By contextualizing Bulgaria’s economic transformations within broader geopolitical and global economic shifts, the chapter provides valuable insights into the structural challenges that continue to shape the country’s contemporary economic landscape, offering lessons that resonate in today’s era of rising protectionism and shifting global trade dynamics.