Continuity mistake: At the end of the movie, Jack parks the car in front of a palm tree and walks onto the beach. The shot changes while he stands there for a few minutes. As the shot changes back to show him walking off the beach, the car is no longer in front of the tree, nor does he drive by during the credits. I hope he enjoys his walk back to Miami.
Revealing mistake: Another movie with plenty of getting in and out of cars, without any car ever being locked or unlocked - in a crime-ridden place as pre-revolution Havana.
Continuity mistake: In the first poker game Jack puts down his cigarette on an ashtray when the game is interrupted. The angle of the cigarette changes from one shot to the next (as if being put with the right or the left hand in different shots). (00:03:00)
Revealing mistake: In the torture scene Roberta's head is stuck into a bucket full of water. When she is released she is not even breathing hard, only in a later shot you hear her gasp for breath. (00:47:20)
Continuity mistake: On the day of the revolution a crowd breaks through the glass doors of the casino. Then the camera is on Jack for a few seconds and when it changes back to the doors all panes are intact again, and the people start breaking them a second time. (02:05:25)
Continuity mistake: When Jack and Roberta meet at the Lido for the first time she has some untidy strands of hair hanging down on both sides. Then she leaves in a hurry, and outside the hotel her hairdo is perfect. (00:20:30)
Continuity mistake: When Roberta leaves the prison she walks out through the middle one of three narrow doors. Seen from outside the doors are at least twice as wide. (00:58:00)
Continuity mistake: On the way to Santa Clara Jack is shot at just after he has just passed a sugar cane field. When the camera angle changes he is still next to the field. (01:21:50)
Continuity mistake: When Roberta is released from prison there is a janitor wiping the floor in the left entrance area. In the next shot from outside the man is gone. (00:58:00)
Continuity mistake: When Roberta and her husband get arrested she is holding on to a brown handbag. When she is released from prison the handbag is black and bigger. (00:57:45)
Continuity mistake: Jack gets beaten up in the hallway when he comes home and gets his lips bruised. When Roberta tends his injuries there is another one on his right cheekbone that hadn't been there after the beating. (01:42:05)
Factual error: When Robert Redford looks at the radio he finds in Lena Olin's car, the radio's ID plate has a serial number beginning with 67-, which means it was paid for by the U.S. government with funds from fiscal year 1967 - eight years too new for a story from late 1958.
Continuity mistake: When Roberta stays at Jack's apartment she looks at two books stacked on the table. She pulls the top one towards her to have a closer look, but in the next shot it's still in the same position. (01:40:55)
Plot hole: Roberta asks Jack to drive her car from the port to the casino to smuggle a transmitter through the checkposts. Since her links to the revolution were known to the authorities, and the chances that her car would be checked were much higher than with Jack's (which eventually also happened) it would have made much more sense if he had transported the transmitter in his own car. (00:08:00)
Continuity mistake: When Roberta is being tortured by sinking her head in water, every time her head is sunk or raised, her hairstyle changes depending on the angle.
