This chapter examines childhood undergrounds as subversive spaces that respond to children’s borderlands and border crossings. Centred on a tale of two childhoods, it analyses children's secret coping practices within very different socio-political contexts and realities. One story is of a boy growing up in communist Czechoslovakia in the 1970s and 1980s, and his relationship to the borderlands between his country and Austria. The other is about a girl born into a German community in Australia, and her linguistic and cultural border crossings. The impact of their borders and border crossing strategies are theorised in relation to children’s ideological settings and forming subjectivities, to offer fresh understandings of childhood border experiences.