Small businesses are a quintessential part of the U.S., making up the large majority of its economy. However, the recovery of these businesses after natural disasters and other events has not been adequately studied. When it comes to smaller communities, this is a large obstacle as the recovery of small businesses largely affects the recovery of the community overall. Prior research on small business recovery suggests a high vulnerability to disasters as well as a low likelihood for owners to mitigate against those disasters; small businesses have a more limited access to capital and knowledge that could help with disaster mitigation/recovery. This study took a close look at the recovery processes and experiences of small, local businesses in the communities of Loiza and Comerío in Puerto Rico after Hurricane Maria in 2017 and ongoing earthquakes. Expanding on surveys of 150 businesses in the combined communities from June 2022, this study incorporated informational interviews of 30 businesses, investigating the challenges that small businesses face in isolated communities along with the interdependence that businesses and communities have. Further, the study looked at how involved stakeholders such as nonprofits and the local/state government have been in recovery efforts and how funding is procured for relief. The results of this study emphasize a stronger level of connection and interdependency at a community level to enhance local business recovery, giving rise to better recovery efforts in the wake of a disaster. It also highlights a gap in mitigation capacity that can be filled by better policy making and heightened awareness on a national scale. These results will also be used to inform lawmakers and planners of the impact of their policies and insight into creating effective and equitable practices for recovery and relocation.