ABSTRACT Rannamaa’s youth novel duology Kadri (1959) and Stepmother (1963), set from mid-1950s to 1961, has retained its appeal across generations in Estonia. This article discusses the novels as a postcolonial Bildungsroman, analyzing the tangle of divergent and often contradictory strands inflecting the socio-political, cultural, and literary phenomena and interconnections operative at the time of their writing. The example of the Kadri novels and their history of publication will show how a particular locus of entanglement need not be static, but rather one transforming in time, and, crucially, one producing propulsions to untangle combined with the dynamics of entanglement and relationality.