This episode was screened for cadets of the United States Air Force Academy as an illustration of the honor code students were expected to observe.
Nick Locarno's character would lay the framework for the role of Tom Paris in Star Trek: Voyager (1995). The same actor Robert Duncan McNeill would play the role. Locarno was supposed to be on Voyager, but legal issues, like having to pay royalties to the writers of The First Duty for every episode of Voyager, made the idea unworkable, so they turned him into a different character. Tom Paris' background and personality were based in part on Locarno.
Wesley has a model of the original Enterprise from Star Trek (1966) in his quarters. It was a pewter and gold replica that the Franklin Mint issued in the late 1980s.
Ray Walston who plays Boothby, later played aliens who take Boothby's likeness in In the Flesh (1998) and The Fight (1999). Oddly enough the last one was VOY's "season 5, episode 19," the same designation for this episode within TNG.
Picard graduated with the class of 2327, which would make him between 60 and 65 years old at the time of this story (2368). When Picard confesses to Boothby that he once considered Boothby a cranky old man, Boothby observes that he was then about the same age that Picard is now. That would make Boothby somewhere between 100 and 110 years old, reasonable, given advances in medicine by the 24th Century. It would also mean that Boothby was probably a young child when Jim Kirk and his crew were exploring the galaxy in Star Trek (1966).