Formal training can play a particularly important role in supporting the internationalization of small and medium enterprises (SMEs). However, the demand for education services by the latter still appears limited. This is due to known structural and cultural limits that are found widely in this type of business and to the fact that the provision of training-especially that which is funded-does not seem to address adequately SMEs' needs; in many cases, such training is not stimulating, because it is perceived as too general. In fact, SMEs do not constitute a single homogeneous group and therefore assistance needs vary among the different types of firms. So, especially in relation to internationalization, it is clear that there are important differences to consider due to the variety of approaches and ways of developing this process. In order to optimize the resources to invest in the promotion of training, there is a need to find a proper balance between providing "viable solutions for all businesses" and offering "targeted responses and tailored services". In such a context, the main objective of this paper is to identify and systematize the variables that most influence the SMEs' training needs related to internationalization by taking into account the differences among them. To this end, an empirical analysis was developed involving a significant number of Italian SMEs by using a combination of qualitative research methods. The results show the critical issues faced by the investigated firms during their internationalization process and highlight some important variables that affect their training needs: export involvement, characteristics of the product/market, characteristics of the company, exporting strategy, and human resources. Based on these variables, the writers identified clusters of firms characterized by similar needs and problems to be faced.