Secretary of State Marco Rubio sanctioned five Cuban companies, despite Havana’s attempts to liberalize.

Rubio leaned into the stick side of the carrot-and-stick approach to Cuba on Tuesday, dashing hopes from the Cuban government that a new move to modernize could spare it from further crushing sanctions. Three of the five companies were linked to the Grupo de Administracion Empresarial, a military-run conglomerate that controls much of Cuba’s economy. The State Department also sanctioned the wife of Alejandro Castro Espin, a member of the Castro extended family.