Transitioning to an infrastructure that integrates a more substantial portion of renewable energy sources into the larger energy portfolio is not effortless or without sacrifice; it has economic, technical as well as social challenges related to the decisions, choices and consequences in trying to establish new energy systems. Those decisions, choices and consequences are highly dependent on the social, economical and environmental context in which they are made. It is of paramount importance to look for a means of involving more sectors in the policy discussions that are taking place in facing the challenges of an increased use of renewable energy. All energy stakeholders should be engaged in discussions about a new energy future. This paper presents lessons learned from experiences with energy stakeholder engagement in Puerto Rico. Both theoretical and practical issues are presented, in the context of a fossil-fuel dependent society which has the added challenge of being geographically isolated from the main sources of fuel. The paper also presents alternatives for broader participation of energy stakeholders in the energy decision-making process as well as education and outreach challenges.