The Cuban university has strengthened its scientific connections with the various social, political, and productive stakeholders. Technology transfer policies have been shaped by historical-economic-social contexts, public policies, and endogenous transformations. Indeed, technology transfer policy frameworks are part of a broader legislative framework for science, technology, and innovation in many economies. Over the last decades, the Cuban government has promoted, regulated, and stimulated the technology transfer framework. However, little is known about the policy framework’s effectiveness. Inspired by this gap, this chapter analyzes the technology transfer policy framework’s evolutionary process in Cuba. This chapter reviews the technology transfer policies framework, the university technology transfer, and the socio-economic transformation during the last three decades (1990–2020) by adopting a retrospective longitudinal. Results suggest that implementing the technology transfer framework should be more proactive and consistent with all participants’ orientation to strengthen innovative companies and expand the public policy framework to the management level of Science, Technology and Innovation System (STIS).