The literature on expatriation typically assumes that cultural and institutional familiarity facilitates expatriate adjustment. This assumption underplays the role of the historical context, especially the influence of painful colonial pasts that often lie beneath such familiarity. In addition, seeking to capture expatriate adjustment as a single measure, such literature does not engage with the differences in the extent to which expatriates achieve cognitive, behavioral, and affective adjustment. Using a qualitative study addressing the work experiences of Brazilians living in Portugal, we argue that to fully understand expatriate adjustment, we must pay attention to the historical colonial relationship between the expatriate’s home and host country. Specifically, we discuss the importance of social representations of history for how expatriates narrate, interpret, and act in response to their experiences. Our research makes two theoretical contributions. First, we explain how historical colonial relationships affect expatriate adjustment and how this leads to adjustment only being partial. Second, we develop a nuanced understanding of expatriate adjustment by drawing attention to its three interdependent dimensions (cognitive, behavioral, and affective), showing that an expatriate may be well adjusted in one dimension but less adjusted in another. We call for organizations to engage more, and more critically, with history.