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Expatriation to support the globalization of trade plays a major role in the success of international business. Failure of international assignments are a high cost to companies who rely on assignees to manage international affairs and can detriment the basic functioning of the corporation. A further cost is the psychological impact on assignees. A well-established reason for failure of international assignments is the inability of the expatriate to adjust to the host location. Using an online self-report survey, various factors were explored for their potential to improve or hinder adjustment. Sample sizes varied between 66 and 105 expatriates (of various nationalities and host locations) for each factor. The functions and sources of social support were explored as a determining factor of adjustment. Despite the potential significant implications for the psychological health of assignees, homesickness has been relatively overlooked in expatriate adjustment literature. Therefore, the detrimental influence of homesickness on adjustment was examined. Social media was considered for its potential to change the dynamics of the adjustment process - allowing greater access to emotional and informational support than before these technologies were available. Finally, agreeableness and openness to experience were explored as predictors of adjustment. A key significant finding was that social support from hosts significantly improved expatriate adjustment. Furthermore, this relationship was mediated by (a reduction of) the emotional manifestation of homesickness. A clearer understanding of the adjustment process may inform selection processes by excluding vulnerable employees, and guide organizations on how to better facilitate assignee adjustment.