This paper reviews the planning history of Sofia since its designation as Bulgarian capital in 1879. It argues that Sofia’s planning has been persistently shaped by two perennial dilemmas—how to reconnect the city with nature and how to define its relationship with the region. In response to these dilemmas, different visions, shaped by both local conditions and dominant foreign theories, were proposed at different times. Some promoted a compact city, while others advocated a dispersed form. The case of Sofia demonstrates the significance of the city-nature and the city-region relationships in the evolution of planning thought. It also points to the difficulties which arise when local ideas of how to organize these relationships are inspired by international models made for cities with different historic experiences.