I am a bit late to this, but the Associated Press reports about how USAID had a program intended to foment unrest in Cuba by sending young Latin Americans into the country.
Beginning as early as October 2009, a project overseen by the U.S. Agency for International Development sent Venezuelan, Costa Rican and Peruvian young people to Cuba in hopes of ginning up rebellion. The travelers worked undercover, often posing as tourists, and traveled around the island scouting for people they could turn into political activists.
In one case, the workers formed an HIV-prevention workshop that memos called "the perfect excuse" for the program's political goals — a gambit that could undermine America's efforts to improve health globally.
I would say this is unbelievably poor judgment but sadly it's too believable. These sorts of operations will inevitably be found out, thus legitimizing the Castro regime's use of the U.S. as a scapegoat. They will not create rebellions, but they could potentially jeopardize worthwhile programs like those intended to fight the spread of HIV. The long-term negatives clearly outweight the positives, as is usually the case with U.S. policy toward Cuba.
USAID issued a vague and platitudinous statement saying the article was mostly wrong while not specifying how. You can choose to believe that if you want, I guess.