Elaine E. Nalley in the Whateley Universe is so notorious for doing this at Whateley Academy that the headmistress gave her the codename Loophole. As a Rules Lawyer, this can cause problems. Eventually, she discovers that the administration believes in Rule Zero.
In another Whateley example, Jobe Wilkin's mandatory school codename is... Jobe Wilkins. It's not just megalomania, given his notoriety as the only sonnote At least at first, this is Whateley after all of the setting's Captain Ersatz of Dr. Doom he figures he's not going to go unrecognized in any event.
Second only to Loophole is one Jadis Diabolik, codenamed 'She-Beast'. She takes very stringent pains to remain on the right side of the rules - and when she sees an opportunity, she'll twist them to take it. At one point she gets around the Whateley 'profit' rules by soliciting a gift worth about 2 million dollars, in exchange for a favour. This runs in the family: her father, Dr. Diabolik, maintains a legal team feared and reviled by innumerable federal prosecutors.
In the Global Guardians PBEM Universe, the 1964 Summer Olympics saw both the United States and the Soviet Union field teams filled to the brim with super-humans. In some cases, the "athletes" were quite obviously superhuman. Olympic officials swiftly closed the loophole that allowed superhuman "athletes" and disqualified both teams before competition actually began.
A big problem in The Salvation War is that nobody has made laws pertaining to the dead, which causes quite a few legal headaches.
Another time, a British colonel tried to take over the command of Free Hell, only to be stopped by Julius Ceaser who points out that because of the amount of people under his command, he is technically a general.
124. Two drink limit does not mean first and last.
125. Two drink limit does not mean two kinds of drinks.
126. Two drink limit does not mean the drinks can be as large as I like.
127. "No Drinking Of Alcoholic Beverages" does not imply that a Jack Daniel's® IV is acceptable.
135. An order to put polish on my boots means the whole boot.
Red vs. Blue has an example of double abuse. Director Church was told he could only have one AI, but nobody said you couldn't torture the AI until it fractured and developed multiple personality disorder, then harvest the personalities as independent AIs. When called on the fact that AIs are considered living beings as far as laws on torture go, Director Church points out that there are many laws about what you are not allowed to do to other people, but no laws about what you are allowed to inflict on yourself, and the AI was a copy of his own mind. It's pretty blatant, because according to season 10 he got his doctorate in the theory of doing it. Did ... nobody think he was serious?
He even gave lectures about it for the Freelancers and their AI, and the only CT and Sigma figured out that he was actually doing it, though they reacted so strongly that they sparked most of the rest of the series.
This very wiki. Tropes that belong in the YMMV section are usually given red bullet points when put into the main section unless the words "in universe" are used. Putting the phrase in universe, regardless of context will remove the red bullet point.
Ain't no rule stating "Web Original" can't have examples from real life, like "most people on the Internet complain about X".
On We're Alive, Kelly falls asleep on guard duty and doesn't hear Latch and Scratch knocking at the door. Michael threatens to kick Kelly out for violating the rules, only for Kelly (a lawyer) to point out that the rules say that while everyone has to take turns on guard duty there's no rule against sleeping on duty.
In the spinoff episode Rainbow Dash Presents Captain Hook the Biker Gorilla, the rules for the flight exam state that a pegasus taking the exam can't be helped by a pegasus (or a bizzaro pegasus). Meaning that the Earth pony Apple Bloom and the demon possessing a unicorn Thrackerzod can help Scootaloo. This being a flight proficiency exam though, they pretty much guaranteed that Scootaloo would bomb the exam, setting the plot in motion.
In one episode of Achievement Hunter's Let's Play Minecraft, Geoff ends up robbing Gavin of a victory when he points out that he can't kill Gavin in the safe zone, there's no rule that he can't take the iron ore he's turning into ingots. Which he does.
Ryan Haywood of the group is known for this. To the point where Geoff had to stop and specifically tell Ryan the only way to kill people.
Gavin pulls this on Ryan during a Let's Play with Grand Theft Auto V. The LP was of them trying to see who could fill up their new Sanity Meter first. Ryan is the first one there, but Gavin declares that he doesn't count because he's already crazy. They're quick to agree to that and that the second one there is the real winner.
In another GTA V Let's Play, Michael ends up winning for his team when his airplane breaks apart and he lands in the water safely, allowing him to make the winning score. Next round, Ryan immediately dives into the water, forcing an Obvious Rules Patch.
"Only Confession Bear?" — All bears "Does Spurdo count?" — He's a badly-drawn Pedobear (not some kind of weird otter like that person thought) so yes "Do hairy men count?" — .... "What about a very small picture of a bear, a — shall we say — micro image?" — No (grudgingly) "How about a funny picture of a bear (not Confession Bear or any other meme-related bear) without words?" — No (very grudgingly)
After the last one the moderator promptly issued a ban on all bear-related pictures
Brother Johnathan: AAAAAAAHHH!! Immediate rules change No bears at all. None. No bear pictures, no bear macros, no bear memes.
In RWBY, Professor Oobleck chews out the team for not following instructions, then turns to Ruby for not leaving her bags at the school. She points out that he never said to listen to him back then, so she didn't. Oobleck concedes that "...she's not wrong."
In Dragon Ball Z Abridged, Android 16 prepares to battle Cell, which confuses 18 as he was designed to fight Goku and only Goku. He points out that Cell's DNA is comprised of 10.78% of Goku's, thus he is a Goku.