It is crucial for Engineering students to be adequately prepared for successful cross-cultural encounters before they embark on any overseas industrial attachment or community service program. This is because they will be exposed to new kinds of experiences that involve informal, incidental, and experiential learning. In addition, the context in which learning takes place is different. Not only will students encounter different cultural norms and values, they have to cope with these at the national, regional, ethnic and organizational levels. Being able to learn positively from cross-cultural encounters is an essential life skill for all engineering graduates today. Hence, they would need to process their experiences within a cultural framework in order to appreciate and enjoy them more. It would also help deepen their understanding and increase their acceptance of cultural differences. At Temasek Engineering School, Temasek Polytechnic, the overseas internship and community service learning experiences for the Engineering students are varied: students can be posted to educational institutions, companies, or support work of NGOs; they could be in Asian or Western countries, in the city or rural areas of first world or third world countries. A fixed curriculum to prepare students for such varied purposes would be limiting in terms of catering to all learning opportunities. This paper outlines the various ways to prepare Singaporean Engineering students for such encounters. This includes the curriculum for face-to-face and online teaching, and the different forms of delivery. This flexible delivery and training model for such diverse needs has worked as the students have found the training useful. The paper ends with the positive feedback from the students and the potential for further development of this program.