Through development of strong strategic capabilities, Chilean companies have increased their foreign presence over the last three decades. Two critical factors influenced this drive to internationalization: (1) limited potential to grow domestically due to the relatively small size of the Chilean economy, and (2) the early start of Chile’s liberalization process compared to other Latin American countries. In this chapter, we examine the strategic capabilities and internationalization initiatives of seven Chilean firms: eClass (e-learning), ALTO (loss prevention), Kunstmann (premium beer production), Forus (premium brands retail), Derco (vehicle distribution), Casas del Toqui (wine), and BeitGroup (children’s clothing). During the internationalization process of these companies, all the firms found it crucial first to transfer strategic capabilities developed at home to another country, and then to successfully adapt these capabilities to the foreign country context. These companies did not seek to acquire or upgrade their strategic capabilities through internationalization.