The intensely active 2017 Atlantic basin hurricane season provided an opportunity to examine how climate drivers, including warming oceans and rising seas, exacerbated tropical cyclone hazards. The season also highlighted the unique vulnerabilities of populations residing on Small Island Developing States (SIDS) to the catastrophic potential of these storms. During 2017, 22 of the 29 Caribbean SIDS were affected by at least one named storm, and multiple SIDS experienced extreme damage. This paper aims to review the multiplicity of storm impacts on Caribbean SIDS throughout the 2017 season, to explicate the influences of climate drivers on storm formation and intensity, to explore the propensity of SIDS to sustain severe damage and prolonged disruption of essential services, to document the spectrum of public health consequences, and to delineate the daunting hurdles that challenged emergency response and recovery operations for island-based, disaster-affected populations. (Disaster Med Public Health Preparedness. 2019;13:5–17)