In the first scene, Lee takes an assumedly freshly-typed letter directly from the typewriter with her mouth. But as she's walking down the hall toward E. Edward Grey's office, a circled error can be seen on the letter.
The 6/7/99 letter addressed to Mr. Ralbovsky has three typos circled, but Grey overlooked the incorrect grammar of the first sentence. There seems to be a word or phrase missing between "requiring" and "issued" at the beginning of the second line. As is, the sentence makes no sense. Also, there are two spaces between "Law" and the case number, and two line breaks instead of one between the paragraphs.
Lee is copying a one page document with the copier cover open. This might be okay if the page was positioned exactly right, but the page is in the middle of the glass instead of in a corner (which is usual) and after Grey tells her "good letter" she accidentally moves the page but continues copying. This would definitely result in askew copies with dark sections.
Lee was bent over his desk and Mr Grey instructed her to pull down her pantyhose and underwear. When he had finished masturbating, she pulled down her skirt but did not raise her pantyhose and underwear. She walked to the door unimpeded and when she was in the bathroom, her pantyhose and underwear were in the normal position.
Mr. Grey slams a letter on Lee's desk and he has circled the
letter 'f' in the word 'knowledfe', which Lee has mistyped. When Mr. Grey brings Lee into his office and makes her bend over to read the mistyped letter she just placed on the desk, we see that the entire word is circled, not just the letter 'f,' as was seen before. Not only that, but the word circled in the letter Lee reads is "illuminatinh", rather than "knowledfe".
When Lee is sitting on Grey's table while keeping her palms over it, during several visits of her friends and relatives, a pot of peas and a pile of books are left over the table. Both the pile of books and the pot of peas seem to appear and disappear in different shots of the scene during a close-up.
Through most scenes in the office Lee wears plain stockings, especially when she is ordered to join Mr Grey in the library. When he asks her "What's going on with the sewing kit and the band aids?" her tights become white and patterned. On a journey home in the back of her Mom's car, the stockings are white and patterned after we had seen her wearing plain brown stockings.
At Lee's sister's wedding reception, Lee's dad is drinking a beer. As camera looks over his left shoulder, he drinks the rest of the bottle with his right hand and his thumb is below the neck of the bottle. The camera shifts to a front view, but although the motion was continuously covered, his thumb is suddenly all the way up the neck and almost touching his lips.
The letter to Mr. Garvey that Lee reads while being spanked is dated June 16, but after she retypes it and carries it to Grey, it is dated June 14. Either this is a continuity error or Grey failed to circle the incorrect date as a typo.
Following the laundromat scene, Mr. Grey is shown circling the misspelled word "genderr" in a legal document; however, when Mr. Grey shows the document to Lee, "gender" is correctly spelled and not circled. Three other typos ("petietion," "coverageis," and "theabsent") are circled instead.
The classified ad at the beginning of the film indicated Grey's office street number was 2640, but a letter that Lee hand-addresses to him later in the film shows a street number of 2540. This may have been an intentional mistake on her part as she had been making mistakes on purpose for several days trying to get Grey to punish her. Besides that, why would she put the office address on an envelope for Grey that she is preparing in his office and thus is not something she'll need to mail? (She did not include her return address on the envelope)
During the shot of Lee with the White Out bottles on the typewriter in the foreground, the reflection (inside the lens?) of the camera operator can be seen - an outline of a head with an arm turning the focus ring.
Depending on what you call a "mountain," Sugarloaf Mountain" is the fifth highest named point in the state of Florida, at 312 feet above sea level. It is also the highest point on the Florida Peninsula. The "mountain" is in Lake County, near the town of Clermont (Where the story is based). Sugarloaf Mountain is the most prominent point in the entire state. So, in order to honeymoon in the mountains by Florida standards, they would not have to drive more than 12 miles.
When Lee gets back in the car after her interview with Grey, the camera angle is in the back of the car looking straight between Lee and her mother. From this angle, one should be able to see Mrs. Holloway's face (otherwise she couldn't see behind the car while driving). Instead, we see the lower side of her head and the space above her right shoulder. To get a line of sight of the rear window with the mirror in this position, she'd have to scrunch down and lean to the right while driving. Worse, as the car drives away, the mirror remains at this cockeyed angle. Also in this scene (assuming they're supposed to be in the actual small city Clermont, FL as opposed to a fictional big city Clairmont, FL) when they drive away from Grey's office, a skyscraper can be seen in the distance (possibly downtown Los Angeles from the south if the scene was filmed in the morning).
While looking for possibly discarded notes in the dumpster, Lee moves a box from Church Brothers Produce, a California and Arizona company. This would probably be an unlikely item to find in a dumpster in Florida.
Lee is bent over his desk and Mr Grey instructs her to pull down her pantyhose and underwear. When viewed in profile we see the edge of a bodysuit across her thigh. It's unlikely to be a tan line because she was completely covered (hiding her scars) while her girlfriends were in bikinis.
The goof item below may give away important plot points.
Errors in geography
In narration near the end of the film, Lee says she and Grey are married and have a honeymoon in the mountains, all in the same weekend. However, since they live in southern Florida, they would've had to drive at least 10 hours each way to reach the nearest mountains in Georgia or South Carolina.