Factual error: When Monk visits the prison for the first time, he is searched, passed, and has a mini-panic attack because people have touched him. Sharona steps forward to comfort him, and she puts her arms around him. This is a very serious breach of procedure and it is not possible for the guards to miss it, because Sharona has not been searched. It's a common technique for trying to pass contraband called 'a touch through' - a person with an item to be smuggled into the prison (drugs, usually), passes them on to a person who has been searched and is therefore 'clean'. Monk would be taken back to the guard's station to be searched again. He would not be allowed leniency because the guards happen to know or to like him - visitor ingress and egress is always done under CCTV and the guard would know he was being watched - quite possibly by someone who doesn't know who Monk and Sharona are.
Factual error: The FBI agent runs a computer check and prints out a list of all the pet stores in San Francisco selling ferrets. But he shouldn't have been able to generate any list at all. Pet ferrets are illegal in the state of California, and are not sold in pet stores there. (00:15:00)
Factual error: While Monk and Natalie are waiting for the mayor to exit City Hall with his aide, you can see a cable car turning around the corner behind them. San Francisco City Hall is located on Van Ness Avenue between Grove and McAllister Streets, and this is at least six blocks from the nearest cable car line (which would be the turntable at Powell and Market Streets). (00:20:00 - 00:26:05)
Factual error: There are a number of unrealistic situations portrayed inside the prison: 1) An inmate scheduled to be executed in less than an hour would not be left so unattended as to require the trustee to yell for help when he went into distress, or to allow the inmate and trustee to exchange objects. 2) A chronic rule-breaker like Spyder, who had just "put a guy's head through a wall," would not have gotten just one day in solitary confinement with no other loss of privileges. 3) The neo-Nazis would not be allowed to wear swastika lapel pins. 4) Death row inmates are not served their last meal by unescorted fellow prisoners.
Factual error: In the flashback where Monk is explaining how the money was stolen, the principal finds the 5 dollar bill he wrote "good luck" on and holds it up for everyone to see. The bill he holds is a 5 dollar bill which was released in 2000, with the enlarged Lincoln. The flashback takes place in 1972.
Factual error: When Monk is talking to Sherry about the painting in the art gallery where the painted woman was going to kill her husband, he says that she has a bruise on her left eye. But the bruise is actually on her right eye. While it is viewable that it is on Monk's left, he would not make that mistake.
Factual error: The woman who accuses Monk of stealing her necklace shouldn't have the necklace inside the asylum in the first place. For both safety and insurance reasons, patients in mental facilities aren't permitted to keep any potentially harmful jewelry, including pins, broaches, earrings, belts, beads and necklaces.
Factual error: Monk inspects the wrecked VW Beetle and notes that "the air conditioning is off." But it's a standard 1973 VW: they didn't come with A/C, and though you could add it, it tended to overstress the little air-cooled engine. Look closely and you can see that this VW does not have the bulky under-dash compressor needed to run an add-on A/C.
Factual error: When Stottlemeyer backs up the video tape at Monk's house, we can hear the sound chattering backwards. Only a huge industrial (studio) machine would do that. Little home VCRs, like Monk's, mute the sound during in-play rewind and fast forward modes. (00:34:30)
Factual error: Randy calls the cabin and gets a "not in service" message. But he should have heard an unanswered ring instead. The FBI agent tore the cord from the wall, which in the US does not generate a "not in service" recording. That only occurs when the phone company cuts off your service due to non-payment or cancellation. (00:30:00)
Factual error: In this episode, when Sharona and Monk arrive to visit his brother, they talk about the swing set. Monk tells Sharona that his father put up the swing when he was 8 years old but this is a much newer swing set. Look at the curved plastic seats: these have come about in the last six to eight years. It also doesn't look at all rusty like a 40 year old swing would.
Factual error: When the flight attendant announces that "they have been asked to return to the gate" the French pilot and his mistress are already celebrating with a glass of wine, but that is impossible since drinks are only served after the take off phase when the plane has reached its traveling altitude. (00:41:15)
Factual error: Monk deflects the policeman's rifle shot and the bullet hits Stottlemeyer's car. But the gun fires just as Monk pushes it aside, and the car is behind them. There's nothing that could deflect the bullet back toward them, so at that angle, there's no way the shot could have struck the car. (00:35:50)