Government influence and direction over a countryâe(tm)s telecommunication infrastructure is determined by policies and regulations designed to provide oversight of how a telecom company should conduct business within the country. While these policies and regulations can range from extremely liberal to authoritarian, a nationâe(tm)s ideology will dictate how governments interact with telecommunications providers and, ultimately, the telecommunications companyâe(tm)s ability to become a viable entity for economic growth. Vast opportunities within the Latin American and Caribbean region exist for telecommunication investors willing to tackle these complex government ideologies. This thesis explores the Caribbean countries of Jamaica and Cuba, where telecommunication has developed in different ways, based on government involvement in the telecom market, and the policies and regulations designed to foster competition, or lack thereof. A detailed analysis into political, business and foreign influence shows that Jamaica and Cuba can benefit directly from private investors willing to venture into these countries. A comparison reveals that policy enforcement affects the balance in relationship between government oversight, telecommunications business investors, consumers, and the economy. Recommendations are provided for policy and regulatory enforcement/updates to better support privatization and liberalization of the telecommunications infrastructure of Cuba and Jamaica.