In Central and Eastern Europe and the Former Soviet Union, housing estates are often associated with inhumane architecture, unwelcoming public space and unending repetition, outcomes that have been attributed to strict design requirements in a rigid centralised system. Due to the uniformity and standardisation of residential housing produced during socialist times, both the design process and its master-the architect-are believed to have played only minor roles in shaping townscapes. This study, situated in the large housing estates of Tallinn, Estonia, challenges these assumptions using analyses of archival material. The study also explains-through first-hand interviews with senior architects who were key players in building socialist cities-the relations between strict Soviet regulations and vital elements of the city building process, including creativity, power and artistry. Analysis of primary source materials highlights an oversimplification of socialist modernism, which suggests more nuanced explanations for town planning outcomes that differ from what strict adherence to Soviet guidelines would have produced. Findings also suggest that regulations issued in Moscow for USSR-wide site planning played a less important role than previously assumed in town planning outcomes in Estonia. International modernist city planning ideals, combined with local expertise (and a willingness to push boundaries yet remain within the political system), strongly influenced town planning practice in the Soviet 'West'.