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(1) Background: Expatriate (expat) teachers, i.e., those living and working outside of their own country, face several unique challenges. Without sufficient protective resources, these challenges threaten to negatively impact upon their workplace engagement and psychological wellbeing, and lead to burnout. In the present study, we utilise the ‘conservation of resources’ (COR) theory to examine the influence of expat teachers’ adaptability (a personal resource) and social support (a conditional/situational resource) on their workplace engagement, burnout, and psychological wellbeing. (2) Methods: A sample of expat teachers (N = 88), mostly working and residing in Middle Eastern countries, completed a series of validated self-report scales to measure each substantive construct. (3) Results: Results revealed that adaptability, but not social support, was a significant positive predictor of both work engagement and psychological wellbeing. There were no significant interaction effects observed. Moreover, neither adaptability nor social support were associated with burnout in this study. Personal resources, such as adaptability, may be more significant determinants of workplace engagement and psychological wellbeing among expat teachers relative to conditional/situational resources, such as social support, according to this research. (4) Conclusions: These findings have important implications for researchers, practitioners, and businesses/organisations, underlining the need to concentrate on strengthening personal resources such as adaptability to improve workplace engagement and psychological wellbeing outcomes among expat teachers. Full article