There is growing evidence that transitions from education to work (and from work to education) can take place several times and occur at different points in an individual's life cycle. This paper's overall intention is to contribute to a deeper understanding of higher education graduates' transitions between education and work shortly after graduation. This contribution draws on the secondary analysis of data collected throughout the employability surveys answered by master's graduates from two universities (Universidade Nova de Lisboa and Tampere University) in different countries (respectively, Portugal and Finland). Aiming at advancing comparative analysis that enables to illustrate the diversity within Europe in this field, a theoretical framework that comprises societal factors, local constellations of institutional systems (in higher education and in the world of work) and individual agency is outlined. Aspects such as the occupational specificities of the degrees, the institutional reputation of the universities and segmentations of national labour markets are also considered in the analysis. Results suggest many similarities but also significant differences within the transitions experienced by master's graduates from the two universities, reinforcing the idea that employability is the result of a complex set of factors and variables within a changing inter-relationship of higher education and work.