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.
Plot hole: When Randy tells Captain Stottlemeyer that the killer shot the train station announcer and took his jacket and ID, the microphone in the room is still active and everyone in the station hears Randy's conversation. If that's the case, then why didn't everyone in the station hear the gunshot? Even if the killer used a silencer, he would have made noise taking the announcer's jacket and changing his disguise, which would sound like a struggle over the open mic anyway, and it would make no sense to turn it on after killing the man. (00:29:00 - 00:30:00)