Mr. Monk and the Captain's Wife - S2-E14
Continuity mistake: In the pre-credits sequence, Karen attaches a clip to the right side of Leland's shirt, but a few seconds later, there is none on his right side. They are all on his left side. They also disappear and reappear.
Mr. Monk Gets Married - S2-E15
Continuity mistake: In the room with the memoirs, Monk turns around and reaches towards a few slightly misaligned books to take one and read it. In the closeup, it's a neatly stacked shelf.
Mr. Monk Gets Married - S2-E15
Continuity mistake: In Dalton's antique store, in the close of the forged map, the "sold" tag is covering part of the state names (mainly the West in West Virginia) and part of the picture. In the wide shot, the tag is now in the corner and not covering anything.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: One of the times the prison guard is attempting to pat down Monk, his hands are approaching Monk's abdomen. After a cut to the next shot, his hands are suddenly around Monk's lower legs. (00:05:55)
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: A fight breaks out in the prison laundry, and Monk crawls into a giant dryer to hide, pulling the door mostly shut after him. But in the very next shot of the fight raging on, the dryer door is visible in the background - wide open. Next shot after that, it's shut again, and Monk sneaks it open to peek out. (00:42:00)
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: When Stottlemeyer and Disher are interviewing Dale the Whale in the bed, in the scene where the fat guy says "Is that a bagel?", Disher's bagel keeps changing size as the camera angle switches, getting bigger and smaller.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: The large blue Nazi/Swastika tattoo on the left side of the head Nazi's neck changes from being neat and symmetrical to uneven during the course of the episode. This is most noticeable when comparing the exercise-yard "you stole the watch" scene to the black-and-white "solving the case" flashback scene.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: When Monk and Sharona talk to Sylvia in the prison library the second time, the books on her desk change in various shots. At first, you see 3 piles of books, all with blue books on top. In the next shot the blue book closest to her is gone. In the next shot, she's straightening a red book next to her, but it goes back to being crooked.
Answer: Notice also that in the opening credits scene when he is touching parking meters her also wipes his hand on his clothes each time he does it.