Puerto Rico's Medicaid program - the health coverage for more than 1.1 million island residents - runs out of its enhanced federal funding on September 30, 2027, and nothing in current law extends it.^[1] Without congressional action, the federal match drops from 76% to 55%, cutting annual federal funding roughly 90% to under $500 million for fiscal year 2028.^[1][2] The analysis behind those numbers comes from Birling Capital, the San Juan advisory firm whose October 5 "Think Strategically" report framed the deadline as "a discriminatory choice Congress makes" - its president, Francisco Rodríguez-Castro, citing the roughly $5,200-per-resident federal healthcare spend in Puerto Rico against a $14,200 national average.^[1] The underlying figures are corroborated across the island's press: NotiCel and Metro both reported the funding-decline projections,^[9] and El Nuevo Día reports Puerto Rico's multisectorial Medicaid committee estimates 860,000 to 1 million residents would lose coverage if the cliff hits.^[3][7] Replacing the lost federal money locally would take as much as $4.849 billion - equal to 35.4% of the island's General Fund - according to the independent analysis Birling cites. The territory's own ask to Congress, filed by Governor Jenniffer González-Colón's administration and PRFAA, seeks $4.815 billion in annual federal Medicaid funding and proposes removing the funding cap entirely, putting Puerto Rico under the same financing rules states use.^[4][8] The pressure is not hypothetical. Hospitals are already losing money, new hospital financing has stalled as lenders decline to price loans against a revenue stream that could collapse in 15 months, and physicians continue to leave the island. Puerto Rico's population has fallen 18.29% since 2000, and the share of residents 65 or older has climbed to 26.8% - an aging, poorer patient base drawing on a shrinking system. On the Medicare Advantage side, where 94% of eligible beneficiaries enroll - the highest participation rate in the United States - fifteen House Republicans led by Rep. Greg Murphy have asked HHS and CMS to set a payment floor for Puerto Rico starting in 2028 at the U.S. Virgin Islands' level, 70% of the Average Geographic Amount.^[5] The joint position presented to Washington - backed by MMAPA, the Puerto Rico Hospital Association and business groups - argues the island has used its five years of enhanced funding to widen eligibility, raise hospital payments and lift physician reimbursement toward Medicare parity. What it needs now is for Congress to treat the September 30, 2027 date as the deadline it has already written into law.^[6]