The mobility regimes in which migratory careers of highly educated women are embedded have a high impact on the invisible sway between privileges and vulnerabilities in situated socio-political contexts. Between 1960s and 1990s, highly educated women began moving on their own, but, despite their qualifications, they nonetheless faced big challenges, some of which have not completely disappeared. Are highly educated migrant women really privileged? This book explores the empirical dilemma between privileges and vulnerability in the framework of conceptual transformations of the highly skilled migration and human mobility in history from the post-industrial era to the present. The book’s subject matter shows an existing sway between privileges and vulnerability in the construction process of the “migratory careers” of highly educated women, which depends on the articulation of macro, meso and micro factors and driving women historically to shape heterogeneous readaptation responses in different geo-political contexts. The case study of the Basque Country in Spain is presented as emblematic reflection of the global economy conformation. The history explored from a gender perspective shows that a critical understanding of the structures of opportunities and constraints influencing women’s mobility is relevant to overcome stereotypes and generate gender-sensitive policies for the socio-economic inclusion of more vulnerable groups.