Goofs

The draughts (checkers) game is cut to suggest that Wormold makes the second move of the game to his right, and that Segura then captures to his right. This is impossible in an actual game of draughts, but if you watch closely, you can see a cut between those two moves where the board configuration has changed.

During the checkers/drinking game, when Capt. Segura removes his gun belt and hangs it on the back of his peacock chair, the holster's retaining strap is fastened over the pistol's hammer. In later shots, it moves to under the grip safety, and then when Wormold removes the Colt from its holster, the strap is already unfastened completely.

At the end, as Wormold and Milly walk across the airport apron, they pass in front of a Bristol Britannia, behind which is a Douglas DC-7. When Segura drives up and they turn round to speak to him, the Britania has disappeared, and they are now directly in front of the Douglas.

When the dachshund is first seen in the banquet scene, it's a black and tan one. Later, when it's begging Guinness for his drink and is licking the drink from his back, it's a red coated one. Then, when it's back with its owner, it's the original black and tan coated one.

"Incorrectly regarded as goof": Segura says during the draughts game "you should have taken me" and then removes a piece and drinks it. In formal draughts all captures are mandatory; however, at the time of the movie, it was common for informal games to contain a "huffing" rule, which says that captures are optional but a player who fails to make a capturing move when one is available is penalized by having the piece "huffed," i.e., removed from the board.

The film is set in Cuba before the late 1958 revolution, but Jim Wormold (Alec Guiness) is shown holding a copy of Time magazine with Harsen Smith of the Chris-Craft Corporation on the cover; this was the May 18, 1959 issue - five months after the revolution.

The plane carrying Wormold to Jamaica is a Vickers Viscount, which has turboprop engines that make a high-pitched whining sound. However, the engine sound that's heard is the grumbling sound characteristic of piston engines.

When Wormold and Hasselbacher are discussing the recruitment of agents in the bar, Hasselbacher, when being shot over his shoulder, is heard to say a line while seen to be drinking deeply from his glass.

While Wormold is talking to the doctor in his ransacked apartment, the shadow of the boom mic moves overhead.

At the end of the film,the aerial footage of the Tower of London has been flipped, resulting in Tower Bridge being on the West of the Tower of London and all traffic driving on the right.

While Wormold is talking to the doctor in his ransacked apartment, the shadow of the boom mic moves overhead.

Millie puts the saddle on the horse backwards. Also, the saddle has no stirrups or girth. The saddle had stirrups on it in the previous scene.