Factual error: In the scene where Matt Damon steals the briefcase from the teacher, he reads a memo listing the Nazi recruits, the title of which is written in both English and German.The German translation is wrong. It begins with the word "The" which should be translated as "Der".

Factual error: When Matt Damon steals the brief case and reads the memo listing the Nazi party members - the title of the memo is set in Arial which wasn't available as a font until 1982. Furthermore, the memo looks laser copied rather than typed. The fact that this is a closeup wiew makes this a rather obvious mistake.

Plot hole: During the 25 years time span of the movie, all of the characters age noticeably except for Clover and Damon. He, miraculously, goes through his teens, 20s and up to his late 40s gaining just a couple of gray hairs and a few wrinkles around his mouth, plus the same young voice from the early days.

Factual error: In the scene where the child who is Matt Damon's character is hiding in the closet before his father kills himself, the child is described as having put on his father's admiral's uniform. The collar insignia, however, is an eagle - the insignia of a navy captain.

Plot hole: Near the film's end, when Edward Sr.'s son, Edward Jr., is about to be married, Edward Sr. approaches his son looking very grim. He is about to tell his son that his fiancee has died. At this key moment, Edward's wife exclaims to her husband, "What have you done?!" Logically, this does not make sense, since Edward's wife, Margaret, has no knowledge (as far as the audience knows) of the Bay of Pigs leak made by her son, nor of her son's fiancee's spy role in obtaining the information. Without knowing this information, Margaret would have no reason to suspect that her husband was involved in some bad incident involving her son's fiancee.

Continuity: On Deer Island during the dinner party before the two lead characters marry, Angelina's character is seen to be carrying a glass of white wine. The scene changes, and the wine is now red when she sets it down on the table.