Expatriates are often presented in the cross-cultural adjustment literature as a homogeneous, broad population. However, recent research that makes a distinction between organizational expatriates (OEs), those who are dispatched by their home companies to international posts, and self-initiated expatriates (SIEs), those who themselves make the decision to live and work abroad, has identified differences between the two groups. The present study compares the cross-cultural adjustment of these two groups of expatriates. Survey results of 179 expatriates in Japan show that SIEs are better adjusted to general aspects of their host country and interactions with host-country nationals than OEs. Suggestions for practice are provided.