Yes, it does happen. Not long ago a Spanish company got in trouble because they operated an hotel in a building that belonged to an USA citizen before the Cuban revolution [1]. A Norwegian company was also charged for using a dock in Cuba, which again, was once American property [2]. I think this kind of thing is becoming more rare since apparently only people who was alive when the Helms-Burton nonsense was passed can litigate, but it is definitely a real danger for anybody doing business in Cuba.

[1] https://www.vozpopuli.com/economia_y_finanzas/retiran-demand...

[2] https://www.reuters.com/business/autos-transportation/us-jud...