CubaIn Jamaica, Ian moved south of the island, producing around three to six inches of rainfall, storm surge and swells that affected coastal communities. While the tropical storm watch for Jamaica was lifted as Ian veered away from the island, a flash flood warning across several parishes remained in effect until the morning hours of 26 September, with localized flooding in some parishes, such as Clarendon, prompting the activation of emergency shelters. In the Cayman Islands, Ian moved south-west of the islands as a Category 1 Hurricane, prompting road and dock closures as debris generated from flooding blocked access points. Power outages and disruption to water systems were reported, however, as of 27 September, electricity and water have been close to fully restored. Ian's rapidly changing track posed challenges for preparedness and response operations in the territory, with preliminary assessments showing relatively minor flood-related impacts, especially in low-lying coastal areas.

On 26 September at 7:00 pm EST, Ian made direct landfall in Pinar Del Río province, battering large swaths of western Cuba as a powerful Category 3 hurricane with maximum sustained winds of 185 km/h. Six western provinces have been affected and more than 61,000 people have been evacuated from high-risk areas. As per WFP-ADAM, close to 600,000 people were exposed to wind speeds of 120 Km/h or higher. According to local and international media outlets, Pinar del Río, the westernmost province of Cuba, bore the brunt of Ian's wrath, with significant damage reported across the province. As of 27 September, Ian has reportedly left at least two people dead and thousands without electricity. In La Habana, one of the six provinces under a hurricane alert, moderate rainfall and strong wind gusts have left several areas in the island's capital of the same name without power. (OCHA, 27 Sep 2022)