Bob has infiltrated Emperor Evulz's side or is possibly undergoing a HeelFace Turn or similar alliance-shifting move. Alice happens to be a prisoner of Evulz. Bob must somehow convey to Alice that he's there, or that he's changed sides, or some other information. However, he can't just go talk to her, because the guards would get suspicious.
Therefore, he makes the guards believe that he wants a few minutes alone with the prisoner, perhaps she needs to be "interrogated." The guards let him into Alice's cell and leave them to it, chortling at the evilness of their buddy's intentions.
Once Bob manages to convince Alice that he was trying to fool the guards (though maybe only after recovering from a vase to the head she was going to use on the real guard to try to escape), he can finally get that information to her, possibly even help her escape somehow.
If the audience has been unaware of Bob's alignment up to that point, this can be the way the Reverse Mole is revealed. It's also highly likely that Bob/Bridget has been putting in place The Infiltration or acted as the Fake Defector.
Not to be confused with the similar, but entirely distinct, Trojan Prisoner Ploy. That's when the heroes try to infiltrate a compound by pretending to be prisoners and/or guards transporting said prisoners.
Compare Merciful Minion.
- In the 2003 anime version of Fullmetal Alchemist, Edward Elric pulls a hilarious version when trying to contact the fake Elric brothers.
- In Mobile Suit Gundam Unicorn, Riddhe visits Audrey's cell twice, first to interrogate her and later to help her escape to Earth with him. Subverted in that the Federation isn't the bad guy and Riddhe wasn't trying to fool the guard, just knock him out.
- In the Blake and Mortimer book The Voronov Plot, Blake, posing as a Soviet officer, tries to pull this in order to contact an imprisoned British spy. Unfortunately, he is interrupted by Captain Ilkor...
- Strontium Dog: Johnny's "norm" sister Ruth uses her status as Minister Kreelman's daughter to get alone in a cell with Johnny under pretense of berating a mutant who tried to oppose her father, as Alpha's true identity is a secret. She gives her brother the gun he needs to escape.
- In the Double Agent Vader Star Wars AU, Vader's interrogation of Leia on the Death Star becomes an example of this trope, with Anakin using the opportunity to discuss her escape options and apologize for not having enough influence to prevent the Death Star being used on Alderaan.
- In Watership Down, Bigwig shows an interest in Hyzanthlay and asks about her, but is told "I'd look elsewhere if I were you, she's a trouble-maker." Hyzanthlay was never imprisoned though, Efrafa was enough to a prison camp anyway to make the point moot. Keeping prisoners isn't in Woundwort's nature anyway.
- Furthermore in the original novel, Bigwig takes advantage of the fact that his position as Owsla gives him freedom of sex, so when he asks for her to be brought to his burrow everyone merely assumes he meant to mate.
- Played straight with Bigwig convincing Blackavar that they are planning a breakout.
- In Django Unchained, Dr. King Schultz asks Calvin Candie to send a particular slave by the name of Broomhilda to his room for a private 'conversation'. While Hildy does speak his native language, Candie clearly assumes he has more than talking in mind, and is happy to oblige. In fact, when Schultz and Broomhilda are alone, he takes the opportunity to reveal, in German so the others can't overhear, that he's come with her husband, the title character, to free her.
- In Gladiator, when Lucilla arrives at Maximus' cell, she tells him "rich matrons pay well to be pleasured by the bravest champions". He has been chained up in preparation for her visit. In fact she's there to tell him there is a growing conspiracy against Commodus, and to ask him to meet a politician who's involved.
- Textbook example in Green Zone, though it turns out the target prisoner is beaten up pretty badly and the conversation doesn't go as planned.
- In John Carter, Kantos Kan, a Helium officer, enters the room where John Carter is being healed (actually, held by Zodangan soldiers). He tries to pull this off by claiming that he's been authorized by the soldiers' leader to "interrogate" Carter alone. The soldiers don't believe him, especially since there's no reason for the leader of Zodanga to trust a task like this to a Helium officer. It's all a ploy, though, for Kan to get close to Carter, so that Carter can steal Kan's sword and take him prisoner. Unfortunately, Carter proves a bit thick and doesn't take the numerous hints from Kan on what to do. So Kan has to literally take out his own sword, put it in Carter's hand, and hold it against his own throat. The Zondangans actually buy that and don't see anything suspicious when Carter performs In a Single Bound halfway across the city while still holding Kan, even though there's no reason for him to hold Kan prisoner at that point.
- Pre-arranged in Ocean's Eleven, when the guy sent in to torture Danny Ocean was set up all along by Danny to show up and pretend to torture him so that he could escape.
- Rusty's posing as a federal agent to rescue Basher from the cops, near the beginning of the film, would also qualify, partially subverted by being done in public (although he does send the arresting police officer off on a wild goose chase to talk to Basher alone and free him from handcuffs).
- Xanth, from The Edge Chronicles, does this for Magda, when she is captured by the Guardians of Night. Slight variation; instead of pretending to be evil for the guards, he just pulls rank on them.
- In Time Scout, one of the characters has been imprisoned for witchcraft, so her rescuers show up pretending to be priests so they'll have an excuse to go interrogate her.
- All the time on Alias. A particularly good example is Irina in "Passage Pt. 2", having pulled a Batman Gambit and aligned herself with Cuvee (which Sydney and Jack think is a FaceHeel Turn). She puts on a good show of interrogating Jack and gets Cuvee to leave her alone with him. She pistol-whips him, but also slips him the key to his cuffs and tells him how to find the nukes they've come to find.
- Babylon 5:
- Subverted in season 4: Garibaldi successfully uses this excuse to get past the first set of guards around Captain Sheridan, but the ones directly outside the cell demand to see authorization, so the rescuers just knock them out. Turns out that was actually the plan all along; asking to get inside was just a ploy to make one of the guards think of the door code so that their telepath could pick it out of his mind.
- Played straight in season 1, when Na'Toth rescues G'Kar from an assassin. The assassin is using pain givers. To free him from the devices she pretends to beat him while actually breaking the pain givers.
- Played straight in season 5, when Londo uses it to break Na'Toth out of the Imperial dungeons.
- On Burn Notice (Mind Games) Michael accidentally exposes an undercover cop while undercover himself. He shoos the others away while he threatens the prisoner, and takes the oppourtunity to mention that he's undercover too and slip the cop a means of escape.
- The sad irony here was that Michael was trying to frame the guy he thought was a monster as an undercover cop to his crime boss. Realizing he has condemned a good man to death, Michael is determined to make sure the cop lives to go back to his wife and kids.
- Doctor Who:
- Played with in "Day of the Daleks": When the Doctor is captured at one of the Daleks' factories, the manager says he'll speak to him alone. The manager is a rebel infiltrator but the Doctor isn't a rebel so doesn't know what he's talking about, and the manager's superior interrupts them before he can get the point across.
- "Day of the Moon": While the Doctor is imprisoned, Canton has body bags brought in containing Amy and Rory, presumably to taunt the Doctor, then has the guards exit so he can interrogate him. Once Canton seals the door, Amy and Rory sit up, and the group go off to fight the Silence in the cloaked TARDIS.
- Sawyer uses this to talk to Sayid in season 5 of Lost.
- M*A*S*H. In "White Gold", Colonel Flagg demands to interrogate a prisoner whom he actually helps to escape for secret intelligence reasons. He then rams his head into a cupboard so he can pretend he was overpowered by the prisoner. Well used to Flagg's insane antics by now, no-one is fooled.
- Gwen tries this in Merlin during the season 3 finale with Sir Leon as the prisoner. She just claims she has "food for the prisoner" and once she's inside the cell, she tells him that she wants to help him escape. They don't know that the conversation is actually being listened to by the bad guys, so they weren't actually alone...
- Stargate SG-1: Colonel Mitchell has to pretend to attack (and then pretend to torture) a captured Teal'c so they can plan their escape in "Company of Thieves."
- Sam and Dean use this in conjunction with the Trojan Prisoner in the episode "Folsom Prison Blues" (S02, Ep19) of Supernatural. Infiltrating a prison to deal with a ghost that has been killing inmates, the Winchesters escape when warden gets them alone after a staged brawl, drops the act that the three of them have been playing all along, and lets the brothers leave through the ventilation system (after a real-fake punch to the jaw from Dean).
- In the Hunchback Of Notre Dame stage musical (that's only been performed in Germany), Phoebus does this with Esmeralda when he allows her to escape.
- At the beginning of Half-Life 2, Barney Calhoun is working undercover for the resistance in Civil Protection, the Combine's brutal police force. When he comes across Gordon, he justifies wanting to be alone with Gordon by implying to another (real) officer that he's going to beat/torture him. Then when the guard leaves Barney and Gordon alone, Barney turns off the cameras and clues Gordon in with exposition and then sends him in the right direction.
- Black Sigil uses this one and twists it just a tad. After being separated from the rest of the group, Aurora and Nephi are alone in Drakus Tat. Nephi (the local King) has to extract information from his loyal subjects (and Aurora is a known enemy of their master, Forbidden), so he declares Aurora his slave and brings her to the dungeon to "break her in". He then calls in one of his minions to lure out the necessary intel in what the minions believe is his "interrogation" of Aurora.
- Metal Gear:
- Near the end of Metal Gear Solid 2: Sons of Liberty, there is a torture sequence reminiscent of the first game that ends with Raiden being released by Olga Gurlukovich. She reveals that she was only helping the Patriots because they were holding her son hostage, and that she was the mysterious "Deepthroat" that assisted Raiden at several points in the story.
- Elisa manages to gain access to Snake's cell in Metal Gear Solid: Portable Ops by, apparently, informing the guard that she wanted to take advantage of him. This apparently freaks out the guard enough that he gives them plenty of space for her to communicate with him unobserved.
- During the Romulan storyline in Star Trek Online, there is a period where you infiltrate the Tal Shiar. One of the first things you have to do is break out a captured Starfleet prisoner, which involves this trope. The actual escape has to wait until the guards come back in, however, due to the method of escape and the need to keep your cover (being seen to shoot and disintegrate the escaping prisoner tends to work better than the prisoner mysteriously disappearing while you were in the room).
- Sokka tried to do this in Avatar: The Last Airbender, when he was deep undercover. Most of the plan wasn't well thought out, so why start now?
- And Suki only ended up hitting him when he made to kiss her before revealing his identity (he was actually hoping to reveal himself with the kiss as a Call-Back to something she had done), which she doesn't react well to.
- He also tried this with Zuko, whispering some information to him while pretending to beat him up.
- George Washington pulled this on a double spy. He had the guards leave him and John Honeyman. Washington then used this opportunity to have Honeyman give false information to Col. Rall and give Honeyman a key so that he could escape from the Guardhouse. Honeyman went to Rall, gave him the false information and that is how George Washington won the Battle of Trenton in 1776.