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Study abroad outcomes are complex and not easy to obtain. In the midst of these challenges, evaluation of pre-departure training for study abroad is needed, yet little is researched. How can we evaluate the effectiveness of pre-departure training when study abroad outcomes are intricate? In this study, by employing Kirkpatrick’s training evaluation model and designing pre-departure training to promote training transfer, we evaluated training impact on study abroad outcomes in a Japanese institution. For evaluation, we employed both qualitative and quantitative measures, such as the Intercultural Development Inventory (IDI), showcase portfolios, and surveys. The findings suggested that training designed for training transfer enhanced the attainment of our study abroad learning outcomes. Furthermore, our attempt indicates that Kirkpatrick’s model is an applicable framework to evaluate pre-departure training for study abroad outcomes.