When flying from the U.S. to Cuba on a participating commercial flight you may use your TSA PreCheck status. When flying from the U.S. to Cuba on a charter flight (non-commercial) your TSA PreCheck will not display on your boarding pass. Unfortunately, this means that you will not be able to proceed through the TSA PreCheck security line at the airport as you normally would. However, if you have Global Entry, please note that it is associated with your passport which will work upon your return into the U.S., as it would returning from any other international destination.
For more information on TSA PreCheck, Global Entry, and other trusted traveler programs, please visit the Department of Homeland Security website.