Adaptation outcomes of skilled immigrants in Canada is hindered by underemployment, meaning skilled candidates are employed in occupations for which they are overqualified. The challenges of overqualification for jobs and its impact on the adaptation process could be influenced by job satisfaction. This study aims at investigating the relationship between underemployment and psychological, sociocultural and economic adaptation of skilled immigrants, and whether such relationships are impacted by job satisfaction and acculturation orientation. From an online survey of 133 skilled immigrants across Canada, the results indicate that a relationship between underemployment, economic adaptation, sociocultural adaptation, and psychological adaptation exists, and that this relationship is not moderated by job satisfaction, but rather mediated by job satisfaction. Findings also suggests that host orientation is a factor that is connected to work experiences and adaptation outcomes among skilled immigrants. Implications and limitations of this study are discussed and recommendations for future research are presented.