The United States restricts dealings with Cuba in two separate ways. One set of rules controls what Americans can do when they visit or send money to the island. The other penalizes foreign companies that make money from land or buildings that Cuba's government seized after 1959. These are not the same rule. A transaction that is legal under one can create serious problems under the other.

What Americans Can and Cannot Do

A U.S. government agency called OFAC manages licenses that allow certain financial activities with Cuba. Think of it like a permission system: the basic rule is "no," but OFAC issues licenses for specific activities it approves.

There are two types of licenses. General licenses automatically cover certain travelers — say, someone visiting family, a journalist doing research, or someone running a humanitarian project. Specific licenses are issued one at a time for activities that don't fit those categories. Someone with a general license can pay for a hotel, buy things for personal use, or send money to relatives.

Which activities get approved has changed with different U.S. presidents. The approved list includes family travel, journalism, academic research, and helping ordinary Cubans. If you break these rules, you face both fines and possible criminal charges.

The Property Law

The second system is a 1996 law called Helms-Burton. According to the U.S. Treasury, it allows Americans whose property was taken by Cuba's government to sue foreign companies that profit from it.

For decades, this law sat unused — every U.S. president from 1996 to 2017 chose not to enforce it. Then, in April 2019, President Trump activated it. Since then, European, Canadian, and Latin American hotels, tourism companies, and phone companies operating in Cuba have faced potential lawsuits in U.S. courts. Even countries allied with the U.S., like France and Canada, have pushed back against this, creating real diplomatic tension.

Why This Matters

Here is the key problem: an American tourist might legally book a hotel room under OFAC permission. But that same hotel could be sued under the Helms-Burton law if it was built on land the Cuban government took over. The permission to travel does not protect the hotel from being sued.

Congress never fixed this contradiction. Instead, different presidents have adjusted the details — making travel rules stricter or looser — but the basic laws stay the same. In 2022, President Biden relaxed some travel and money-transfer restrictions. But the framework itself has not changed.

For people working in international business or compliance, the takeaway is straightforward: OFAC permissions cover what Americans can do, and Helms-Burton covers what foreign companies can do. These are separate legal questions.

The bigger picture is that U.S. Cuba policy tries to do two things at once: put pressure on Cuba's government through financial and property rules, while leaving room for travel, money sent home, and humanitarian aid that helps ordinary Cubans. Whether this approach actually works is something experts genuinely disagree about. What they do not disagree on is that these two legal systems are different and operate independently.