Studying abroad can be stressful due to culture shock and various other difficulties. However, with the current prevalence of information communication technology, we can surmise that study abroad difficulties should be minimal. Since it has been shown that an individual’s personality is highly associated with their internet use behaviors, it would be interesting to determine the effects of personality traits on the relationship between internet use motives and perceived study abroad difficulties. Data were collected from 1870 volunteer study abroad students in Taiwan. Hierarchical regression analysis revealed that when controlling for the effects of age, gender, duration of stay, student status (short-term exchange or degree-seeking), and internet use motives (online benefits, habits, and facilitation), the personality trait neuroticism consistently showed significant relationships with the various study abroad difficulties. Moreover, moderation analyses revealed that all the personality traits except conscientiousness showed significant interactions with internet use, while simple slope comparisons showed significant differences between the high personality traits and their lower counterparts. In sum, an examination of the moderating role of personality traits in the relationship between internet use and study abroad difficulties may be useful for preemptively identifying at-risk students.