A hilarious variation occurs, where the crew of the mercenary ship effectively avoid any litigation by becoming legally appointed bounty hunters, hunting members of the lawyer collective. They could still be sued if anyone apart from them used non-Collective attorneys, but Massey is the only non-Collective lawyer we've seen, and he's a member of the company.
Tagon (Having just shot someone's lawyer-drones): Get as mad as you want. You're going to have a hard time suing me.
Presumably, after this strip there's now a company policy regarding air vents, where there wasn't one previously.
Tailor is a clothing fabrication robot given to Captain Tagon by his father. The captain hates robots, his father, and isn't particularly crazy about new clothes, so he refuses to agree to any fittings. Tailor freaks out about not being able to fulfill his purpose, until the company doctor points out that the captain is responsible for clothing the entire company—therefore, Tailor can fulfill his purpose by creating clothing for her.
Tailor: I'll have to padlock a couple logic gates, but I think it can work.
More recently, the IFCC used this trope to their advantage via their deal with Vaarsuvius: they never said their brief ownership of V's soul would take place after their death.
And later still, Roy exploits a loophole in the rules for the Godsmoot, allowing him to attempt to kill the High Priest of Hel, negating the goddess's vote:
Wrecan: But the rules of the Godsmoot are unambiguous: A bodyguard who raises arms against the priest of another god must be put to death immediately! Roy: Are there any rules about what happens if a bodyguard attacks their own priest? Wrecan: ...No.
A little later, that loophole gets closed when the High Priest of Hel transfers his position to another vampire as he leaves to dominate the Dwarven Elders. Since Roy wasn't designated as that vampire's bodyguard, he's not allowed to kill her. However, he quickly exploits another loophole to ensure that Malak's staff doesn't fall into their hands.
Roy: The Order of the Stick is not responsible for any damage that may occur during the delivery of unholy relics.
Black Mage: We're going to grab the non-fabric of this anti-space time and rip it a new one. Red Mage: Is that even possible? I'm not sure this place actually exists. Black Mage: Then there's no rule that says we can't.
In the webcomic Brat-Halla, there ain't no rule saying that a god dueling another as a tie-breaker in the Pantheon Games can't call in his independently sentient, disembodied eyeball in a Humongous Mecha to help him. For extra amusement, after t'other god tries to cite its absence in the rules, that there ain't no rule saying you can, the eyeball in its mech comes in and cites the rule in question. Linksky.
According to The Whiteboard, there is no rule forbidding the use of cross-country skis in paintball games. Doc checked very carefully.
Emily wins her first race in Misfile. Ain't no rule against driving 25 mph once you're ahead of your opponent!
Aki Alliance: There's a rule against wearing a headset to receive outside help during a Scrabble competition. Oddly enough, there's no rule against wearing a headset to give outside help to someone else during a Scrabble competition.
The Constitution didn't provide for insane bunny senators and therefore did not lay down a rule about what to do when one goes missing. In Prickly City, this matters.
Eerie Cuties: The bonus story of vol.2's print edition has Blair trick Kade and Ace into playing a game of "StripTrivial Pursuit" against Layla and Brooke, during which, he rigs the game so he can see the girls naked. Layla guesses wrong on her next turn, leaving her no choice but to take off her bra. However, Brooke saves her by cupping Layla's breasts from behind. When the boys object, she counters:
Brooke: (smug) "Ha! You boys haven't won anything yet!"
Kad: "No fair!"
Ace: "That's against the rules!"
Brooke: (smug grin) "I'm technically made of snakeskin, so I count as clothing!"
George: You're a robot! You're not allowed to kill humans! Protoman: That only applies if I think he's a human, which I don't.
Tristan pulls this in Angel Moxie so she can get away with a Non-Uniform Uniform in the form of striped stockings. She even recites the specific rule, noting that while there are limits on what kind of socks can be worn, stockings are allowed as an alternative and there are no such limitations for them.
Take one tabletop-gaming Rules Lawyer from our universe and drop him into an RPG-Mechanics Verse with the instructions to "grant our side victory by any means possible". You now have the plot of Erfworld.
Some of the natives are extremely adept at this as well. For instance when Thinkamancer Maggie asks her thickheaded, jerkass overlord Stanley if she can give him a suggestion. When he says yes, he immediately takes a Suggestion spell in the face.
In one of Black Hat's schemes, he takes the observation that standard internet server racks and beehive frames are both 19 inches and have similar pitches and runs with it, noting that most web hosting TOSes* Terms of Servicedon't mention beehives in what's not allowed. The Alt Text calls back to the example listed above, noting that most TOSes also don't prevent dogs from playing baseball in the server facility.
This strip has Black Hat repeatedly trying to go around rules on meta-wishes in very convoluted ways. None seems to work.
Played with in #1593, where Beret Guy seems to believe that stealing a base in baseball is loophole abuse. His reaction is, "Everyone's real mad but I guess they checked the rules and there's nothing that says he can't do that."
Fruit Incest double-subverts this one in "Rule". There's no rule against a duck playing on the school soccer team, but there is a rule that every player on the team must be enrolled as a student. But there's no rule against a duck being enrolled as a student, either.
Another case: Robots are hard-coded to obey and protect humans. When one Jerkass boss fakes a heart attack in order to get to a meeting on time, this response forces them to abandon Florence in freezing water in the middle of a hurricane. With a few tips from Sam, the robots retaliate by "protecting" the boss from things that are bad for him, like coffee, sugar, and stress from meetings.
Sam: I've never heard maniacal laughter from a robot before. It feels good to have brought something new and wonderful into the world.
uu from Homestuck does this to Calliope (UU) during their chess game by making his king and queen wear hats so UU thinks they're the opposite pieces. As he points out, there's technically no rule against it, and he never had either of them move in a way they shouldn't have... Calliope is, naturally, very unimpressed, and when she plays on only to lose to him she Rage Quits rather impressively.
Immortals in El Goonish Shive are only allowed to guide and empower mortals without risking the wrath of other immortals. Those are the rules, here are the loopholes:
Helena and Demetrius tricked consent from a younger Susan and Nanase by giving them the false impression that they were the only two who could stop a monster. This ended up causing Susan enormous emotional damage, which later deeply angered Jerry, another immortal, when he learned her story.
Chaos has twisted the rules into pretzels by forcibly empowering unsuspecting mortals and pumping enough power into them to make them susceptible to suggestion bordering on Mind Control. Her son notes when explaining this, "even immortals have loopholes." We find out that this is an even bigger loophole later, because Chaos wasn't the one who did that. Another immortal left clues that made her son think it was her, thus remaining hidden for months.
An immortal can only attack a mortal in self-defense, but according to Jerry Grace is lucky he's a "wise and jolly" immortal ("Like Santa Claus!") because making a threat display, like the way Grace did, towards a more flinchy immortal would have been enough to make that immortal panic and attack the offender.
As it turns out, the rules aren't an agreement between immortals, but a sort of species-wide curse they cast on themselves. If an immortal breaks the rules, the other immortals don't decide to fight them. The other immortals automatically gain knowledge of what happened, and the power to work together to force the offending immortal to reset. The immortals wouldn't have agreed to this if there was some way to break the rules on accident, so only the opinion of the immortal breaking the rules matters on deciding whether or not something is breaking the rules. This is why Chaos can get away with so much loophole abuse: She's crazy and thinks everything she's doing is within the bounds of the rules.
Subverted when Voltaire vows not to attempt to kill Elliot. Mr. Verres points out that if Voltaire successfully kills Elliot, it's not an "attempt." Voltaire disagrees, and thinks that's a really stupid loophole, but rewords his vow to close that loophole anyway.
Chaos increased the overall magic concentration in Moperville to incredibly high levels, allowing novices to use spells that they should never be able to. When Sarah learns of this, she immediately realizes that Chaos basically "empowered" the entire town. Furthermore, when Chaos realizes she has to fix what she did, she needs help from a mortal (which falls under the "guiding" rule), since she's not allowed to "dis-empower," even though she was behind the original empowering.
Magic itself is a quasi-sentient force that wants to be used and known about, but not widely known about or able to be used by many, which would seem to be contradictory goals since there's nothing stopping magic users from telling others about it and providing them the means to use it themselves, nor can magic simply go away. But there's nothing saying magic can't change the way it works, so that previous methods of using it are rendered useless, and only a few rare individuals will be initially able to use it again. Chaos/Pandora witnessed the last time this happened several centuries ago.
Parodied in "Last Meal", where a convict asks for his last meal to be the executioner, and they have to comply.
Executioner: "On the one hand I'm mad, but on the other hand wow what a loophole."
Peonio, a power hungry fairy from Fairy Dust, wants to bribe two trolls into staying on his island, where only tiny sized peoples live. When one of them says that he would stay if he had women of the proper size, using his friend as a standard, Peonio brings him women the size of a dragon hatchling that was given the same name as his friend.
Only two people can enter the arena at a time. Keyword being enter. Meaning that Goten and Trunks can get away with fusing as Gotenks, entering the arena, and eventually defusing and competing as two people cause hey, only one actually entered the arena. Which happened with two incarnations of Gotenks. This also accidentally happened to U9 Videl when her Z Sword broke and released the old Kai in it. Since he came from the sword he was ruled an ally and allowed to stay in the arena.
Much later, U3 Raichi takes this trope up to eleven, where he summons the Frost Demons, all of Planet Vegeta AND the previously defeated combatants. Doesn't stop U13 Vegeta from instantly wiping a few of them out.
A few characters have taken advantage of the rule made to prevent excessive hiding or leaving, that if the judges cannot see you for more than thirty seconds you forfeit. XXI uses it against U16 Vegetto, trapping him in another dimension where time ran differently just to be sure and U18 Uub uses it on U11 Buu, vaporizing him down to one small final bit and then putting that bit in a container before he could reform. Technically the judges could not see Buu, and thus he lost.
In MMBN 7 The World Tournament Dr. Hikari realises in his match against Ryu & Cosmoman that Cosmoman's Infinite Cosmos attack locates the enemy and fires off an infinite number of meteors at them, but Cosmoman needs to actually see the opponent for it to work.
In the fantasy comic strip Yamara, a toad familiar is tasked with bringing a newly-revived ex-vampire her first non-blood meal in centuries. The cleric forbids him from serving her meat, while another character threatens him with punishment if he offers her fruits or vegetables. His solution is to serve her cream of mushroom soup.
In Digger, Descending-Helix made a deal that he be paid for his work by making him and all his descendants immune to divine interference and prophecy. A few thousand years (and the laws of genetics) later, his great*n-granddaughter gets roped into that business anyway, thanks to the interference of a prophetic slug. His ghost admits that he had neglected to fill that particular loophole.
Paranatural has hitball, dodgeball under a different name so as to get around the dodgeball ban. In the game itself, a girl is covered with duct tape to avoid getting out, because you'd only be out if a ball hits you then the floor.
Stand Still, Stay Silent: Mikkel pulls two of these in a row in Chapter 10, after Sigrun refuses to take him on a mission. He simply leaves on his own, claiming that Sigrun never told him not to leave the Cat-Tank, she just told him he couldn't go with her. When Tuuri points out that there is a rule against leaving non-immunes without a guard, he indicates Lalli, who is both immune and a capable fighter... and is so deeply asleep that multiple people moving him around and touching his face has failed to wake him.
In Ménage à 3, Matt comes to believe that he's put Kiley off men for life by lying to her, which lead to them breaking up. So he swears to himself that he'll get her back, and that he won't sleep with other women from now on. However, he's bisexual — so this doesn't put a stop to his (very energetic) sex life.
In Goblins, demons making a deal with mortals have to obey the terms of their deal to the letter, or they are revoked and the demon is horribly punished. When Saves a Fox and Dies Horribly are searching for the Orb of Bloodlight, they find that it is guarded by demons. One demon holds an orb and promises it in exchange for a mortal soul. Dies, knowing his Meaningful Name is going to have to trigger sooner or later, immediately agrees to the terms so that Fox can at least get the orb. Of course it's a fake. Too bad for the demon, she agreed to give the orb in exchange for a mortal soul. Due to the artificial hand that Klik gave him, a bit carelessly, Dies Horribly actually now has two souls. So the deal is revoked, causing Dies to return to life with his prophetic death having already technically happened, and the demon gets hit with a heaping dose of Laser-Guided Karma. Thus, the heroes accidentally abuse Loophole Abuse, canceling out deliberate Loophole Abuse.
Gunnerkrigg Court: When it comes time to choose a new Court Medium for dealing with the Forest, everyone is sure it will be Annie who gets the position, and Coyote has been not-so-subtly hinting that he wants it to happen as well. The Headmaster, however, wanting to curb Annie's behavioral problems, names Andrew the Medium instead. Coyote immediately turns it around on the Court and appoints Annie as the Forest's Medium for dealing with the Court, declaring her an honorary member of the Forest (as she had lived there for a summer). The Court has no right to interfere in Forest matters, so Coyote and Annie get what they want anyway.