The Trump administration has maintained and intensified its maximum pressure approach toward Cuba through Executive Order 14380 in late January 2026, which declared a national emergency and authorized tariffs on third countries supplying oil to the island, followed by Executive Order 14404 in early May that expanded secondary sanctions on Cuban regime entities, military-linked firms, and sectors including energy. These measures have enforced an effective oil blockade, contributing to documented fuel shortages, blackouts, and economic strain on Cuba as of May, with no subsequent executive actions, Treasury licenses, or State Department announcements indicating sanction relief. Recent statements from U.S. officials have tied any potential engagement or limited assistance to demands for political and economic reforms by Havana, while designations under the new sanctions program continue. This sustained tightening of restrictions, rather than easing, underpins trader expectations against any oil sanction relief announcement by the end of June.