Puerto Rico is an U.S. unincorporated territory and its political situation, economic downturn, significant migration to the U.S. mainland, and technological capabilities create a very unique combination of challenges and opportunities for the healthcare system in the country. Some of them are related to incorporating healthcare information technology (HIT) best practices from the U.S. with the local culture in mind. The current study aims at investigating the current state of technology adoption in Puerto Rican healthcare and provides some policy recommendations for improving the implementation process. We argue that a more technologically advanced healthcare system will improve clinical decision support, will increase prevention, and will ultimately provide better health outcomes for Puerto Ricans. We draw upon some best practices in HIT implementation in the U.S. but we suggest that the local context and culture be taken into consideration in order to achieve more effectiveness and more positive results.