Disaster struck Puerto Rico on September 6th, 2017, when Hurricane Irma, a category 5 hurricane, breached the islands. Communities had no time to recover as Hurricane Maria, an even bigger threat, reached land not more than two weeks later. These two disasters happening in quick succession led to a devastating death toll of 2,975 people and caused a total of $90 billion in damages. This had been the most devastating disaster to hit in over 100 years. The people of Puerto Rico are still recovering to this day and are trying to find solutions to creating community resiliency. This thesis will focus primarily on what makes a community resilient and how to apply this to other Caribbean nations. Not all Caribbean islands face the same challenges and each one has its own identity. To assume that all islands are the same would be irrational. Additionally, this thesis will look at how a community can shift from being unconventional to very functional. Throughout the recent years, there has been a shift in design and function toward creating communities that are more sustainable, durable, and resilient. While this shift can occur easily in more modern societies, those that lack the resources to do so will continue to struggle unless proper support can be given.