This brief provides an overview of the status of the health care systems and Medicaid programs in Puerto Rico and the U.S. Virgin Islands (USVI) about one and a half years after Hurricanes Irma and Maria struck the islands in September 2017. The hurricanes exacerbated the territories’ existing economic and health care challenges by accelerating outmigration of residents and health care providers and destroying homes, schools, health care facilities, and other infrastructure. After the storms, the territories’ Medicaid programs have served as important resources for addressing residents’ health care needs, but they have operated under longstanding financing challenges. This brief focuses on these challenges and includes KFF analysis of the implications for the territories’ Medicaid program finances, as most of the temporary federal Medicaid funds provided through the Affordable Care Act (ACA) and disaster relief are set to expire at the end of September 2019. The other U.S. territories (American Samoa, the Commonwealth of the Northern Mariana Islands, and Guam) also face challenges tied to the scheduled expiration of ACA funds.