Originally comprised of two eponymous stories, later editions of the book added two others.
- "Octopussy": A crime from the past of a retired major in the British Army catches up to him.
- "The Property of a Lady": A top spy for the Soviets must be identified during an Auction for a piece of Fabergé jewelry.
- "The Living Daylights": Bond must stop a KGB assassin from killing a fellow MI6 agent who is trying to escape from East to West Berlin.
- "007 in New York": Bond is tasked to warn a girl in MI6's payroll of her double agent boyfriend.
In the movie side of things, the first story was incorporated into the backstory of the thirteenth James Bond film, with a hint of the second story as well. The first story's backstory of Bond being raised by a Swiss ski instructor was also incorporated in film twenty-four. The third story was grafted onto the beginning of the fifteenth film. A character name, Solange, from story no. 4 was used in Casino Royale (2006), and its plot inspired the finale of Quantum of Solace.
- Black Market: In order to sell his gold without attracting unwanted attention, Smythe turns to a pair of Chinese brothers who have underground connections in Macau.
- Driven to Suicide: After their marriage went completely sour, Smythe's wife killed herself by overdosing on sleeping pills. Smythe himself is also in process of doing the same, albeit by the slower path of drinking himself to death.
- Hollywood Density: Averted. The gold stash Smythe finds is so heavy that he can barely even get it back to his jeep without collapsing as it weighs about half as much as he does. When he needs to take the briefcase of gold through customs without getting searched, he needs benzedrine pills and an iron will to avoid looking like he's carrying anything heavier than papers.
- It's Personal: Bond took the job of finding Smythe because the man he killed was a Parental Substitute for him in the past.
- Leave Behind a Pistol: Bond tells Smythe that he has a week before the authorities will apprehend him. He comes to the realization that Bond is giving him a chance to kill himself, thus keeping things tidier for the paperwork.
- Nazi Gold: During World War II, Major Smythe learned about a stash of two Nazi gold bars, and shot the mountain climber that helped him in the back of the head because of them. He's been living off of them since.
- Stealing from Thieves: Smythe absconds to the Caribbean with his wife and the gold directly after World War II. Despite the initial success, it's portrayed as a rather melancholy affair, as the money fails to alleviate either Mrs. Smythe's overdose on pills or Smythe's drinking problem.
- Suicide by Pills: How Smythe's wife kills herself using sleeping pills after their marriage takes a turn for the worst.
- Villain Protagonist: The whole story takes place from Smythe's perspective, with Bond appearing for only about ten pages of a substantially longer story, or from his point of view, for a few minutes close to the end.
"The Property of a Lady":
- Feed the Mole: The money from the auction is going for a mole within MI6, whom they are routinely feeding with false information.
- Glasses Pull: A very subtle example, done by Maria's KGB handler using a pair of sunglasses. It's his pre-arranged signal to the auctioneer that he's not going to bid up the price anymore, and Bond uses it to start the process of getting him expelled from London as persona non grata.
- The Mole: Maria is one for the KGB, and has been from the moment she started working for MI6. Played with, in that they knew she was a mole all along and have been deliberately feeding her false/useless information as part of a ploy to draw her handler into the open.
- Rule of Drama: When Bond hears that nobody in England does "going, going, gone" bit in auctioning anymore to provide a chance for last-second bidders, he finds it pitiful, since he thinks that it "adds to the drama".
- Unspoken Plan Guarantee: Subverted: Bond outlines his plan for spotting Maria's KGB handler in painstaking detail...and it goes off without a hitch. He doesn't even confront the antagonists for a final showdown, simply informing the proper authorities to have him picked up. The drama instead comes from the task (identifying the handler among an auction crowd) being incredibly hard by the simple fact that most bidders use a subtle pre-arranged signal with the auctioneer for privacy, which Bond has to try and spot in the crowd without making it obvious that he's looking.
"The Living Daylights":
- Blasting It Out of Their Hands: Upon seeing that Trigger is the female cellist he saw earlier, he shoots the gun out of her hand instead of killing her.
- I Need a Freaking Drink: Bond calms his nerves with a glass of whiskey. When his spotter protests, he notifies that he's not the one who is supposed to kill someone.
- More Dakka: Bond and his handler are dismayed to find that Trigger is armed with an AK-47, in a time when such assault rifles were relatively uncommon and full information was unknown to many people (Fleming mistakenly calls it a "submachine gun").Bond: They're going to do a saturation job after all. Perfect for range. We'll have to get him pretty quick, or 272 will end up not just dead but strawberry jam.
- "Not So Different" Remark: Not that this is what stopped him, but Bond is conscious of the sniper as "an enemy agent with much the same job in her outfit as he had in his" whom he expects to be in far worse trouble after.
- Senseless Violins: Bond suspects that Trigger brought her gun to the opera house in her cello case.
- Shown Their Work: As background research, Fleming corresponded with Captain E.K. Le Mesurier, secretary of the National Rifle Association at Bisley for information and to correct some of the more specialist areas of knowledge required for sniper shooting.
- Title Drop: The story ends with Bond quipping about scaring the living daylights out of "Trigger".
- Wouldn't Hit a Girl: When Bond sees through his scope that "Trigger" is the woman he has become fond of during the assignment, he chooses to shoot her Kalashnikov instead of killing her.
"007 in New York":
- Big Applesauce: The entire story is pretty much a description of places in New York from Bond's point of view.
- Unspoken Plan Guarantee: Bond's extensively detailed plans for his stay all come to naught when it turns out his rendezvous location doesn't actually exist.