Continuity mistake: In 3-7 "Employee of the Month", Joe Christie says he was with Monk when he got the news of Trudy's death. He said Monk had been laughing, and that he never heard him laugh again. In this episode Monk and Stottlemeyer get called to the scene of a crime, a women's clinic. In this episode there is a flashback to the exact same location years earlier and to Stottlemeyer getting the phone call about Trudy's death. He and Monk were working a case that day and Joe Christie was not present.
Continuity mistake: They interview Jimmy Belmont in prison, who complains how Monk sent him there for killing Randy's uncle in 'Mr. Monk Visits a Farm.' However, in that episode, Monk tricked everyone (including Randy) into believing Randy had solved the murder.
Continuity mistake: The edition of the San Francisco Chronicle with the headline on Jimmy Cusack's death is dated April 1, 2006. However, at the end of the episode, which is a few days later, the newspaper with the front page photo of Stottlemeyer arresting Ron Neely, is dated March 24, 2006. In addition to the fact that the date of the arrest is a full week before the date of the murder, April 1, 2006 fell on a Saturday, when the episode says the murder was on a Monday night. (00:05:05 - 00:40:25)
Continuity mistake: When Sharon asks Sydney's old flame about the mugging 20 years ago, the glasses in front of them are full when they are being filmed from behind Sydney's ex, then are half empty being shown from behind Sharon, and in the next shot they are full again. (00:32:00)
Continuity mistake: When Monk attempts to steal the truck at the gas station and grabs the sleeping driver's keys, he drives the truck in circles and then stops. When he stops, the truck is exactly parallel to the end of the concrete slab where the gas pumps are located. However, when the police arrive, the truck is now at a different angle with the back of the truck now being closer to the end of the concrete slab than the front. The gas station attendant would not have moved the truck himself as the police would have told him not to touch anything at the scene.
Continuity mistake: When his wife visits Stottlemeyer in his office he fills the running waterfall with coffee, but later in that scene when he holds her hand to promise her that he will investigate the the old man's death the waterfall is empty again. (00:04:40 - 00:07:10)
Continuity mistake: When Natalie puts out the fire with the extinguisher, the nozzle is still pushed down when she uses it, but when she puts it on the table, in the next shot the nozzle is fully extended. There are a number of times during the scene, when Monk is trying to figure out how to use it, where the nozzle's position keeps changing between shots.
Continuity mistake: Whilst Monk is being introduced to the long standing winner on the show a stagehand is adjusting the microphone on his jacket with both hands. As he says "Are you almost done?" the shot changes and the stagehand is just using his left arm to adjust it. The stagehand then pulls his arm away but the next shot he is adjusting the mic again and using both hands to do it. It keeps changing throughout the rest of the scene.
Continuity mistake: In the scene where the two guys are playing chess, the guy with the black hat knocks over the chess pieces after losing. He then starts scrambling up the pieces and leaving his hands near the chess board. When the shot changes to a wide shot of Monk walking away the guy suddenly has his hands on his head.
Continuity mistake: In the cemetery scene, Stottlemeyer approaches the grave of the 17 year old open case hit and run victim. The dates on his grave are 1980-1997. But in Dennis Gammill's confession letter in the end, it says he killed the boy in December 1998.