''Webcomic/TheOrderOfTheStick'' might be the only comic in existence that can have some hilarious meta/Fourth Wall jokes (and a couple of [[LampshadeHanging Lampshadings]]) and then successfully pull off a heart-wrenching [[spoiler:death scene]] ''in the same page''.

'''Note:''' Please keep the examples sorted in chronological order, as to avoid repeats.
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* ''Start of Darkness''-- The second scene consists entirely of [[spoiler:[[DeathByOriginStory Redcloak's entire family save Right Eye being massacred by the Azure City Paladins]]]].
* ''Start of Darkness'' -- when the wizard Dorukan rages against Xykon for his imprisoning the soul of Lirian within a magic stone. Of course [[MagnificentBastard Xykon ends up kicking his ass and imprisoning him within the very same stone]], where Dorukan's soul meets up with Lirian's.
-->'''Lirian:''' Dory? Dory, is that you?\\
'''Dorukan:''' Yes, my love. I've failed. It looks as if I am to share your prison forever now...\\
'''Lirian:''' [[YouAreWorthHell No, no... not a prison anymore.]] ''(they embrace)''
** As they are together, you can also interpret it as a SugarWiki/{{Heartwarming Moment|s}}, though.
* The climax of ''Start of Darkness'', particularly [[spoiler:Right-Eye]]'s [[FamousLastWords last words]]. [[spoiler:"Goodbye, Brother." "Goodbye... Redcloak."]] ''Major'' DownerEnding.
** Especially since he called him Brother or Big Brother throughout ''Start of Darkness''. [[spoiler:Until he lies dying as a result of his betrayal. Then it's just "Redcloak".]]
** Also because throughout the story, Right-Eye criticizes Redcloak not correcting Xykon on his name, since he considered the nickname to be a demeaning sign of domination.
* Lampshaded in [[http://www.giantitp.com/comics/oots0084.html #84]] -- although it doesn't show on the page, the title of the comic is: "Saddest. Comic. Ever."
* [[http://www.giantitp.com/comics/oots0131.html #131]]. Haley putting on her mask to the world...
* [[http://www.giantitp.com/comics/oots0311.html Internal Dialogue]]:
-->'''Haley:''' But I'm a rogue...
-->[[spoiler:'''Haley:''' ...Hiding is my best skill.]]
** Also [[http://www.giantitp.com/comics/oots0316.html here]], with Haley battling with her own sense of self loathing as the countdown comes for Southern Continent New Year, debating whether to risk kissing Elan, and by the time she hesitantly reaches out to him, some random Azurite has already grabbed him. The last line of the strip is in her (at the time) custom cryptogram, but says, "happy new year."
* [[http://www.giantitp.com/comics/oots0375.html This comic.]] Poor Durkon.
* [[http://www.giantitp.com/comics/oots0367.html This comic.]] And then [[http://www.giantitp.com/comics/oots0387.html later this]].
-->[[spoiler:'''Elan:''' My {{evil twin}} brother is going to kill my-- my Haley! And she's all unsuspecting and defenseless and, and, and Haleyish!]]
* [[http://www.giantitp.com/comics/oots0393.html Haley having to helplessly watch as Nale convinces Elan that she is evil]]. Well, until she [[spoiler:gets her voice back]], that is.
* Played straight in [[http://www.giantitp.com/comics/oots0443.html #443]].
** The line "Wait-- why do I feel like we were supposed to be somewhere?" in the last panel of #444 just hammers it home.
* Three Words: [[http://www.giantitp.com/comics/oots0445.html "Oh Buddy Roy"]]. Appropriately set to one of the most heartbreaking folk songs in human history.
** "Oh Buddy Roy" is even more tear jerking if you read it while listening to [[http://www.youtube.com/watch?v=nUTzTWaLW7Q this video]]. Read along with the flute that starts out at about 1:18. It's heartbreaking.
** One of the forumites is an operatic tenor, and he recorded a rendition of the song which he posted on the site. It was gorgeous.
** [[http://www.youtube.com/watch?v=XCYLNj0KXcE Here's a rendition]].
* [[AlasPoorScrappy Miko Miyazaki's]] [[spoiler:[[http://www.giantitp.com/comics/oots0464.html last moments]]]]. Notably, out of the nearly 800 strips that exist as of this writing, this is the ''only'' one that doesn't have any jokes in it.
* Also a CrowningMomentOfHeartwarming: Roy [[spoiler:[[http://www.giantitp.com/comics/oots0496.html meeting his younger brother, who'd died very young, and playing blocks with him]]]]
-->[[spoiler:'''Eric:''' Hi Roy! wanna play blocks with me?]]\\
[[spoiler: '''Roy:''' ''(a tear running down his face)'' More than anything.]]
** [[spoiler: Then you find out that they made the block castle 34 times without Roy noticing because he was enjoying it THAT much.]]
* At first, [[http://www.giantitp.com/comics/oots0527.html this strip]] just looks like a gag involving Roy being frustrated as he tries to communicate with Haley. But then you think about it, and about how normal she treats the whole scenario, and you realize that for months, she's been fighting and struggling on her own, and keeping herself going by talking to all that remains of her former leader and friend, because she cares about him that much, misses him that much, and needs him that badly. It's kind of sweet and kind of horribly sad.
* "[[http://www.giantitp.com/comics/oots0550.html Sweet Dreams, Monster-san.]]"
* [[http://www.giantitp.com/comics/oots0593.html "...I'll take my chances that the afterlife... won't have any punishment worse... than not being with you..."]]
* After [[spoiler: Kubota's disintegration at the hands of Vaarsuvius]], Elan reveals the details of [[spoiler: Therkla's death]] and how he feels personally responsible. But Vaarsuvius doesn't care about it, and criticizes Elan for forgetting about Haley, which infuriates him. Commentary in the hardback books reveals that, while Elan may not have approved of V [[spoiler: killing Kubota]], he probably would have gotten over it because the man was evil. But V's treatment of [[spoiler: Therkla]] appalls Elan and makes Elan, who once dressed up as a wizard because Vaarsuvius was so cool, want nothing more to do with him.
** [[http://www.giantitp.com/comics/oots0598.html #598]]. Elan's speech to [[spoiler:Therkla]]. Particularly her tombstone. '''[[spoiler: Therkla]]'s Headstone:''' Here lies [[spoiler: Therkla]] ???-1184 She would have [[spoiler: made a pretty cool girlfriend, too]].
** And later, what Elan [[http://www.giantitp.com/comics/oots0647.html did in response.]]
* Vaarsuvius [[spoiler: keeping the soul splice and leaving his/her family behind to try and fix everything else.]]
** [[http://www.giantitp.com/comics/oots0623.html Or just before]] [[spoiler: It's a memory of her invisible and unable to cast spells, as she bumped into terrified, fleeing soldiers on the way to the ship. She was forced to watch as they pleaded for her help before getting torn apart by the horde of Hobgoblins...]]
** And [[http://www.giantitp.com/comics/oots0679.html later]] [[spoiler:[[ItsNotYouItsMyEnemies not contesting his/her mate's request for a divorce]] to "[[GiveHimANormalLife let them live the peaceful life of a baker's family]]" [[IWantMyBelovedToBeHappy rather than put them in danger]] ]].
* O-Chul's final conversation with the Monster in the Darkness.
** And O-Chul's [[spoiler:escape from Xykon's prison, and MITD's reaction, finally calling him by his name.]]
-->'''O-Chul:''' You may not know exactly what you are, but I do.
-->'''MITD:''' You do? Really? Then what am I?
-->'''O-Chul:''' [[SugarWiki/HeartwarmingMoments A good man.]] Farewell, my gentle friend.
-->'''MITD:''' Wait, Mr. Stiffly! Come back! Mr. Stiffly! MR. STIFFLY! O-CHUL!
* When O-Chul [[spoiler:escapes]], he takes out Redcloak's right eye. As punishment for his failure, Xykon forbids him from using Regenerate to restore his eye. So now he's got an eyepatch over his right eye and one working, left eye. In one comic, just before he gives a big speech, he is seen looking in a mirror. His reflection shows his face reversed, so he sees [[spoiler:Right-Eye. His brother]]. And it dawns on you that that's who he'll see ''every time'' he looks at his own reflection. He just stands there looking at the mirror for a panel or two, and says, simply, "It'll all be worth it. You'll see."
* Elan's one-two revelation that his father is not only [[http://www.giantitp.com/comics/oots0759.html evil]], but also [[http://www.giantitp.com/comics/oots0763.html highly savvy.]]
** Even worse, he's taking the [[RuleOfDrama rules of drama]] that Elan loves so much and twisting them to the evilest applications imaginable. The worst part is his last line, "we're going to tell the best story EVER!"
*** Because, going by the rules, it's 100% true.
* [[http://www.giantitp.com/comics/oots0768.html Haley's reunion]] with her [[spoiler:father Ian]] [[http://www.giantitp.com/comics/oots0769.html starts well,]] but then [[http://www.giantitp.com/comics/oots0770.html descends]] into letting his [[http://www.giantitp.com/comics/oots0771.html trust issues]] [[http://www.giantitp.com/comics/oots0772.html split them into separate ways.]]
** Also, the death scene [[spoiler:of Haley's mother]] that started the guilt complex [[spoiler:of her father]] in failing to save an important life.
** [[http://www.giantitp.com/comics/oots0774.html The last 3 panels of this page]]. No other comment necessary.
-->''"No, Dad. I didn't mean what I said. You raised me well."''
** The potion only works on ''lies''.
* [[http://www.giantitp.com/comics/oots0783.html What the hell is wrong with you, you stupid oaf? You moron! Kill me already!"]] Even Roy admits how wrong the scene is... and then Tarquin ends it.
** "Enor...don't you see? It has to be you. It has to be. You have the Victory String." Remember that [[http://www.giantitp.com/comics/oots0777.html 6 strips prior to this]], Gannji had given him the very same string so Enor would have the bravery to face his opponent. [[spoiler: Little did either of them know that they would face each other.]]
** And a little while later, it's revealed that even Belkar, the Order's TokenEvilTeammate, [[http://www.giantitp.com/comics/oots0807.html was affected by it]]. [[spoiler: Specifically, he released the arena's previously-featured dinosaur to disrupt the fight (which allowed Enor and Gannji to escape) because he heard Roy say that watching the two fight was like watching someone be forced to duel his own puppy. Cue Belkar's point of view, where he sees Enor's face replaced by [[MoralityPet Mr. Scruffy's head]] and his own head replacing Gannji's.]]
* Thanh and Niu during [[spoiler:the fall of the [[http://www.giantitp.com/comics/oots0827.html Resistance.]]]]
-->'''Niu:''' [[spoiler:...You're the bravest man I've ever met.]]
-->'''Thanh:''' [[spoiler:And you're the slowest woman. Run!]]
* Tsukiko may be an evil creepy murdering bitch, and probably did deserve what happened to her, [[http://www.giantitp.com/comics/oots0830.html but it's no less horrible to watch.]]
--> [[spoiler:"No! Stop! You don't have to do this, little ones! He just wants you to think you have to! You can- AAAGH!!- You can fight back! Resist! No! NO!! Don't you- AAAGH!!- Don't you understand? I love you all! I love you! Why don't... you love... me?"]]
** Then a couple of comics later when Xykon's rounding up Team Evil to go after the next Gate he casually asks where "what's her name, the chick with the pig tails" is. No matter how colossally misguided it was, she did love him, and it's a little heart-wrenching to realize how little he thought of her.
*** Especially as it happened because she was trying to provide him with concrete proof of two things that he ''really'', '''really,''' '''''really,''''' would have wanted to know; [[spoiler:[[http://www.giantitp.com/comics/oots0830.html A: that the Snarl won't give him the power he desires, and, B: that Redcloak is manipulating him.]]]] And she only did it because she genuinely loves him. [[spoiler:AlasPoorVillain]].
** And when the rest of Team Evil finds out what happened to her, the only one actually upset about it is the Monster in the Darkness. When one of the Demon Roaches asks him why he's upset, he explains how sad it is that Tsukiko really just wanted to be loved.
--->'''Demon Roach''': So what? Who cares?
--->'''[=MitD=]''': Exactly. That's why I'm sad.
*** It's also possibly a bit of the YouBastard to people who disliked her "thinks she's in a romance novel" character.
* While Elan is trying to figure out how to feel about his father:
--->'''Elan''': I thought it was tough to figure out how to feel about Nale, you know?
--->'''Roy''': What's so tough? He's a villainous jackass!
--->'''Elan''': [[ThickerThanWater But he's still my brother!]]
--->'''Roy''': I think you're overemphasizing the importance of biological ties, Elan. Nale has tried to kill you three times!
--->'''Elan''': I know that! But sometimes when I was little, I would walk in on my Mom crying about having lost a nail. And now, I don't think she was upset about missing hardware '''at all'''!
* The consequences of the Familicide spell Dark Vaarsuvius used [[http://www.giantitp.com/comics/oots0843.html finally catch up with the Order]]: "The propensity of both dragons and humans to [[HalfHumanHybrid breed outside their species]] is well documented." [[spoiler:''The entire Draketooth family was related to a Black Dragon.'' [[NiceJobBreakingItHero Which will now prevent the Order of the Stick from directly finding the Gate]]. Even worse than that, Familicide did not only kill the Draketooths. It killed anyone that was related to them by blood. And the Draketooths happened to be scoundrels who propagated by seducing random bystanders and absconding with the resulting children. All those bystanders are now dead - along with every living member of ''their'' families! ''And there is no reason to believe that they're an isolated case.'' What really sells it is V's expression. The Order may forgive him/her, but s/he [[MyGodWhatHaveIDone never will]].]]
** And throughout V's explanation of why [[spoiler:Familicide was so awful, we see a montage of several bystanders and their families being slain by it.]]
** When's the last time we ever saw V cry? Not when his/her mate was threatened, not when s/he was served divorce papers, not when s/he saw his/her children's legs broken, house burned down and mate crucified on a tree. This hit him/her ''hard.''
* Failing her save against a Holy Word, Sabine [[http://www.giantitp.com/comics/oots0860.html apologizes to Nale]] and gives him some last advice, along with "I love you... forever." However, Nale was deafened by the same attack and can't hear her, so he doesn't understand what's happening.
** She also warns him not to do anything rash - and not to trust his father and cohorts. {{Foreshadowing}} as Nale decides to kill Malack.
** Even sadder [[spoiler:since these are the last words she says to him while he's alive]]... and he can't hear them.
* While it's outside of the strip, Rich's injured hand and the responses people have given wishing him well.
* [[spoiler:Mr. Scruffy]]'s useless attempts to stop [[spoiler:Malack from killing/vamping Belkar]].
** On a related note, [[spoiler:Malack's desperate attempt to preserve his friendship and form a truce with Durkon, only to get rebuffed primarily because of his vampirism.]]
* [[spoiler:[[http://www.giantitp.com/comics/oots0877.html Durkon's death]]]]. Belkar's gonna be pissed.
** Made either better or worse by the fact that [[spoiler:he died happy, because it meant he was finally going home.]]
*** [[spoiler:As a vampire.]]
*** [[spoiler:What make it especially sad is that he died mainly because he refused to compromise and he put his faith in the wrong people: Malack who betrayed him but was willing to walk away and Thor who he worships wholeheartedly but who wasn't even paying attention when he died.]]
** In the aftermath of that, Belkar trying to rush off and warn the others, only to get vertigo due to his injuries. So he ''starts crawling''.
*** His shocked disbelief that ''he'' is still alive while [[spoiler:''Durkon'' is turned into a vampire]]. Deep down it really seems like he thinks his life is worth less than [[spoiler: Durkon's]].
*** Before his fight with Malack, Belkar said that he had something to live for, which is why he will survive. [[spoiler: Durkon's last wish before he died was for Malack to not harm his friends because they have more to live for than him]].
* Remember the old example that out of 800 strips, only one had no jokes? As of this posting, there are over ''900'' comics, and there is a second strip with no joke. It's [[spoiler: Durkon's death, and him saying that he's going home]].
* Right afterwards: [[spoiler:Belkar, barely alive, crawling back to the rest of the Order and breaking the news -- and Roy almost attacking him, thinking it was another one of his tasteless jokes.]]
** Made worse on [[spoiler:Belkar]]'s side by the fact that Roy only comes around to believing him when Haley points out that [[spoiler:she doesn't think he COULD make up a story of heroic sacrifice.]] Harsh.
** Made worse if you believe that [[spoiler:Roy's anger isn't due to it being, well, ''Belkar'', but due to his desperate attempt to deny what has happened to his best friend.]]
** As it is the first comic in which [[spoiler:Durkon is absent ever since he showed up to save Belkar]], it will also be the first one that will make you cry seeing [[spoiler:the joint "Thanks, everyone" message from Roy, Haley, Elan and Durkon at the very end of the page]] (if it didn't start happening at [[spoiler:the latter's actual death]], that is).
** [[spoiler:"He just walked in there and saved my life and got straight up murdered for it."]] Talk about tearjerkers...
* [[http://www.giantitp.com/comics/oots0881.html "This is it, isn't it? This is us losing. This is what us losing looks like."]]
* After [[spoiler:Durkon dies]], Roy is not pulling his punches. Elan's expression right after this exchange is especially heartrending:
-->[[spoiler:'''Roy:''' And as of now, we don't even have any spellcasters!]]
-->[[spoiler:'''Elan:''' Roy, I'm a spellcaster.]]
-->[[spoiler:'''Roy:''' YOU DON'T COUNT!!]]
* More unlikely Belkar tearjerkery action: [[http://www.giantitp.com/comics/oots0881.html Belkar acknowledges his own limitations and sociopathy, even seeming to lament them.]] Similar to the example above, this one line of dialogue almost lends a smidgeon of tragedy to Belkar's character.
-->"Hurting people is the only thing I'm good at."
** The reason he had to say such hurtful things? [[spoiler: Durkon getting turned into a vampire]] ''crushed'' Roy's resolve. Roy, who was willing to keep going despite the insane odds, was ready to give up. That's how badly he was hurting. [[CruelToBeKind And the only way to keep him going was to hurt him again]].
* Qarr taunting Vaarsuvius with the horrific consequences of his Familicide. V is curled up in a ball sobbing when Qarr calls him "history's worst mass murderer". Blackwing isn't any help either since the only rebuttal he gives is that "history isn't over yet", which means that Blackwing technically ''agrees'' with Qarr.
** From the same comic, Vaarsuvius casually mentioning that [[spoiler: "Master Thundershield" should have Raised one of the Draketooths by now. Cringe-inducing since we know how sad V will be when (s)he finds out about Durkon. (S)He may even go through another HeroicBSOD if it occurs to hir that it might not have happened had the Draketooths still been alive when the Order & the LG arrived at the pyramid, or if (s)he had been present for Durkon's fight with Malak.]]
* It's clear from #885 that Roy is ''really'' guilt-tripping over [[spoiler:Durkon's death]].
* [[http://www.giantitp.com/comics/oots0887.html #887]]. Everything has gone wrong. [[spoiler: Durkon's dead, V is lost, Tarquin and Nale are winning, and Xykon is on his way.]] The Order is surrounded on all sides, and there's no where left to run except unknowingly into a happy ending [[LotusEaterMachine created by an illusion]].
** The happy ending illusion itself. First, long-dead secondary characters are alive and well in it due to the Order members not knowing that they're dead. Second, it's pretty obvious that the person (or someone if it's collective) whose illusion is shown [[spoiler:would have preferred Durkon to be alive and Belkar to be dead rather than the other way around]].
** Everybody under the spell gets their happy ending. Haley is shown rolling in gold and helping her father take over the Thieves' Guild, which Roy wouldn't know anything about. Elan makes peace with his family, something the other two don't see as a happy ending. Roy gets to rub his swords-are-better-than-magic philosophy in his sister's face, something the other two wouldn't know would be a part of his happy ending. Clearly, there is no one point of view; everybody under the spell gets their happy ending. Belkar is dead, and is presumably killing monsters in the abyss. That's his happy ending.
*** And his cat's dead too. Which means either one of his teammates found the cat too evil to keep around, or Belkar wants the only thing in the world he cares about to stay by his side.
*** At Belkar's funeral, Roy and Varsuuvius are ''walking away''. They don't care enough even to stay as long as Elan has.
** What's even worse; NONE OF THIS CAN EVER HAPPEN!!! It's been shown multiple times in the comic that the UnspokenPlanGuarantee is almost a law of nature. The only plans that have a chance of happening, are the ones the audience doesn't know about until it's too late. This spell means none of what we see has a chance of happening. They won't be able to hold Redcloak down so Roy can fight Xykon. Roy won't be able to use the special move his grandfather taught him which had, until now, remained [[UnspokenPlanGuarantee unspoken]]. They can't throw Xykon's phylactery into the ocean/lava. And Elan won't get his dinosaur ride.
*** Elan got his dinosaur ride in #923 so there be be hope for this yet.
* In #888 is somehow both tearjerking ''and'' hilarious, as we see that Elan thinks it might be a good thing if his parents got back together... the imagery and dialogue are just hilarious, but the implications make you want to cry.
* [[spoiler: In #889, Elan breaks the party out of the illusion by admitting the truth that he's been hiding from. He can never fix his family, his dad and brother are irredeemable. His dream of his family being together again will never happen.]]
** [[spoiler:[[BreakTheCutie "But it doesn't matter what I want! It doesn't matter what any of us wants! What's real... is that my family is screwed up and broken. And it's not going to just get magically fixed, ever."]]]]
* A small, but very gut-wrenching, one as Roy [[spoiler:sees the vampire Durkon for the first time.]]
** Another gut-punch as [[spoiler:the newly freed from thralldom Durkon goes to heal Roy like he usually would in a situation like that... and ends up hurting him instead. Ouch.]]
* Small, and short, but Nale is horrified, angered, and hurt when [[spoiler: Vampire Durkon just casually gives Zz'dtri a NeckSnap.]] Mind you, the two were [[VillainousFriendship actually friends.]]
* In #913, Elan's reaction when he sees [[spoiler:his father Tarquin kill his brother Nale]].
** Nale's monologue right before [[spoiler:Tarquin stabs him to death]]. He only wanted to be free from [[spoiler:his father's]] shadow.
*** You don't notice it at first due to his professionalism, but Tarquin takes a moment to confirm Nale's motives before resigning himself to [[spoiler:killing Nale to avenge Malack. In fact, Tarquin explained to Nale that the arc was his chance to prove himself. Tarquin didn't want to go through with it, but he couldn't ignore Malack's death.]]
*** Can also be read as [[spoiler:Tarquin realising that Nale will never be his pawn and no longer holds any use for him.]] It doesn't really matter what interpretation you choose, both are definite tear jerkers.
**** [[spoiler: Tarquin made a Freudian slip when told by Nale that his father and Malack were going to kill him anyway. In [[http://www.giantitp.com/comics/oots0849.html #849]], Tarquin reassures Malack by telling him to look forward to the '''end''' of the mission. He was going to off Nale no matter what. His telling Nale that he was only appearing Malack and was going to convince him to let Nale live later on was a lie, if this is true, though.]]
*** #914 [[spoiler:confirms the latter, as Tarquin goes on about how Nale was just a B-class villain and that Elan had outgrown him. Tarquin's indifference to killing his own son makes it even more of a tear jerker.]]
*** [[spoiler: To add to that, Tarquin saying that Elan would be the only one who didn't desire Nale's death... Cue the last panel showing a ''very'' pissed off Sabine who just witnessed her lover's death through the IFCC's TV set and destroyed it in a fit of rage.]]
---->'''Sabine:''' ''(to V's soul as it returns to his/her body)'' Knock 'em dead, elf.
*** Sabine was banished downstairs earlier to Durkon's Holy Word, and her last words to Nale before she went was her screaming that she loved him but he was deafened by the same Holy Word. [[spoiler: Those ended up being her last words to him... and he never even heard them.]]
**** It doesn't help that Qarr hangs up on her when she calls and he never relays her words to him either.
*** Reread "Happy Ending" and "Dream Wedding" knowing all this will happen.
*** As [[spoiler:Nale's ashes scatter in the wind, Elan grasps hopelessly at them, begging for his brother to come back.]]
* "I'm not a twin anymore."
* When Roy and Vaarsuvius are discussing the details and moral ramifications of [[spoiler: V's DealWithTheDevil and subsequent actions,]] Roy relates an anecdote about another wizard who got too reckless with his experiments. Putting two and two together, he is referring to the time [[spoiler:his father]] accidentally killed [[spoiler: [[http://www.giantitp.com/comics/oots0496.html his brother.]]]] The conversation also reveals that Roy blames himself for Durkon's vampirism.
* Durkon [[spoiler: is not the vampire. he's been trapped inside the whole time, watching the vampiric personality play his friends like fiddles while serving Hel. And Roy has no idea he's working with his friend's jailer towards the destruction of his friend's home!]]
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