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* ''Franchise/AceAttorney'':
** ''VisualNovel/PhoenixWrightAceAttorney'': Mia's death near the beginning of the game is a bit different from this trope's norm in the sense that you don't really get a sense of how awesome she was until after she dies- though it still hits hard as she's the player's co-counsel in the tutorial and you first encounter her little sister crying over her dead body. In any case, Redd White is quite likely the most hated villain in the series who isn't a final case villain.
** ''[[VisualNovel/PhoenixWrightAceAttorneyJusticeForAll Justice for All]]'':
*** Case 2-4 becomes a Player Punch right off the bat, but the salt is only sprinkled in the wound later on when you discover that Matt Engarde is a ruthless criminal who couldn't care less about you and Maya, whose kidnap he ordered.
*** There's the part where the player is forced to accuse [[TheWoobie Adrian Andrews]] of murder, and force her to talk about some deeply traumatizing topics (such as her mentor's suicide) by threatening to out her ''own'' suicide attempt and codependent tendencies. She's ''completely innocent'', but can be convicted of murder if you don't make the right choices.
** ''[[VisualNovel/PhoenixWrightAceAttorneyTrialsAndTribulations Trials and Tribulations]]'': In case 5, when Dahlia Hawthorne starts cackling about Maya's apparent suicide, and how she can't be punished for it because she's ''already dead''. Even given that you've most likely figured the true plot out already by this point, the anger generated by this scene is part of what makes Mia and Phoenix's resultant HannibalLecture such a SugarWiki/MomentOfAwesome for the series.
** ''[[VisualNovel/PhoenixWrightAceAttorneySpiritOfJustice Spirit of Justice]]'': All throughout case 5, [[spoiler:Dhurke Sahdmadhi was]] your main companion in this case. You get to know him personally and find him not that much different from Phoenix Wright himself. Late in the case, you find out [[spoiler:that Dhurke Sahdmadhi is DeadAllAlong. This revelation [[DespairEventHorizon is the]] DarkestHour in Apollo's life]].
* ''VisualNovel/ActingLessons'': Wanted to be in a poly-relationship with Megan and Melissa? [[spoiler:One of them dies in a house fire at the end of Episode 6. And you have to choose which one to save, '''and only one of them.''']]
* ''VisualNovel/AnalogueAHateStory'': As you read the logs, you find out that at one point, the Pale Bride stopped speaking during her time on the ''Mugunghwa'', even to the one person she trusts the most. [[spoiler:Towards the end, you read a log file called "Forever Silenced', and you learn the source of her apparent muteness: her adopted parents ''forcibly cut her tongue out'' in order to get her to behave and to fulfill an ArrangedMarriage. Even *Mute, who holds *Hyun-ae/the Pale Bride with contempt, is horrified to learn this. It's not hard to see why she eventually snapped and killed everyone on the ship, including herself.]]
* The first case of ''VideoGame/AviaryAttorney'' looks a whole lot like the first case in any of many of the ''Franchise/AceAttorney'' games -- defending a [[GoodLawyersGoodClients young girl]] from a charge of murder and instead pointing to a SmugSnake who had motive, could have easily committed the crime, and who gets furious and threatens you while on the stand. [[spoiler:She soon reveals that she's guilty after all and says that pinning it on a business rival was a stroke of genius. Now she and her father get the shares held by the murder victim ''and'' the innocent businessman who's about to be executed.]]
* ''VisualNovel/CauseOfDeath'' has a few of these, notably [[spoiler:Tasha King's death]] in 3-7, [[spoiler:Phil Morris's death]] in 4-8, and most certainly [[spoiler:Ken Greene's HeroicSacrifice]] in 8-6. These examples are notable for making you want to absolutely destroy their respective killers afterwards (that is, [[spoiler:Ryan Orville]], Herman Hartnell and [[spoiler:Kolo Zargoza]]).
* ''VisualNovel/{{Clannad}}'':
** When Nagisa and Tomoya want to confirm Fuko's situation by trying to get her older sister Kouko to meet her, Kouko ends up staring ''straight through Fuko'' and she says to Tomoya, "''That girl stopped breathing yesterday.''"
** And then there's Nagisa herself who dies in her good ending from child birth - this is necessary to get the best ending (i.e. saving Nagisa).
* ''VisualNovel/CorpseParty'':
** Early on, Naomi and Seiko unwittingly step into a pile of gore. It's played for dark laughs, but later on, we find out that the body belongs to their friend Mayu.
** And then there's of course the big Player Punch regarding Seiko herself. It turns out that Seiko's death was not a suicide, as initially believed, but a case of [[TomatoInTheMirror Naomi]] becoming possessed by [[TheCorruption the Darkening]] and putting a noose around Seiko's neck. Not only does Naomi realize that ''she'' is at fault for her best friend's death, if the player doesn't manage to [[GuideDangIt do the right thing]] and get the best ending, Naomi will attempt to commit suicide by hanging herself.
** The first chapter of ''Book of Shadows'' revolving around Naomi and Seiko, with the former realizing that [[GroundhogDayLoop they've been in this situation before]] and that her fight with Seiko resulted in her friend's death. Trying to avoid the fight doesn't work, and so Naomi has to end up finding Seiko before she dies. The true ending of the chapter is a cruel HopeSpot because Naomi succeeds in rescuing Seiko from her death, only for Seiko to freak out when seeing Naomi and running away, before falling down a flight of stairs and [[OffWithHisHead losing her head]].
*** Immediately after seeing Seiko die again, [[BigBad Sachiko]] appears and mocks Naomi -- and the player -- for thinking they could avoid the terrors of Heavenly Host. Sachiko reveals that any person that died in the school is ''fated to repeat their deaths'', no matter how many times you might try to change things. And those deaths tend to be worse than the original one.
* ''Franchise/{{Danganronpa}}'':
** ''VisualNovel/DanganronpaTriggerHappyHavoc'' has the obvious gut punches whenever one of the characters you've come to care for turns out to be the next victim... or the murderer.
*** Chihiro's final Free Time event, when Naegi [[ButThouMust has no choice]] but to [[spoiler:recommend Chihiro ask Mondo for help getting stronger -- which leads Chihiro right to his death]]. This is only accessible in a NewGamePlus, so the player ''knows'' what will come of this...
*** Sakura's final Free Time event reveals that the person she could never defeat [[spoiler:was Kenichirou, her boyfriend, who was terminally ill. Given only six months to live, he fought to survive... yet enough time has passed before the events of the game that he's likely long since passed on]]. Thankfully, this is neutralized come ''VideoGame/DanganronpaAnotherEpisodeUltraDespairGirls'', in which it's revealed that [[spoiler:Kenichirou is still alive, at least up to the beginning of the game, which takes place several months after the end of the first]].
** ''VisualNovel/Danganronpa2GoodbyeDespair'': Case 5 forces you to [[spoiler:vote for NiceGirl Chiaki as the culprit, even though she didn't even mean to kill the victim]]. ''Twice.'' The other students desperately trying to stop you, coupled with Hajime himself practically being on the verge of tears, makes the ordeal absolutely ''[[TearJerker heartrending]]''.
** ''VisualNovel/DanganronpaV3KillingHarmony'':
*** There is a hefty slug to the gut in the very first trial, where it's revealed that the culprit is none other than [[spoiler: Kaede Akamatsu. Yes, ''the protagonist herself is the murderer this time''. After you select her as the culprit, [[DecoyProtagonist the P.O.V shifts to Shuichi]], a detective who is not only afraid to reveal the truth, but also a LoveInterest for her]]. You then have to push to establish the culprit's guilt, and it's made painfully clear that the player character ''really'' doesn't want to go through with it. Nor, most likely, does the player. Then the game hits you again by having the culprit's execution be used to demonstrate how much more [[DarkerAndEdgier brutal and agonizing]] the executions are in this game. Also, [[spoiler:Kaede's shot put ball didn't hit Rantaro, but the Mastermind whacked him after it fell, then tampered with the crime scene. Yes, [[MiscarriageOfJustice Kaede died for nothing]]. [[YouCantThwartStageOne No, you can't keep her from being executed]]]].
*** Much later, the game comes back for seconds. [[spoiler:The culprit of the fourth chapter is none other than GentleGiant Gonta, who was manipulated into doing it by Kokichi and ''doesn't even remember that he did it''. Just like with Chiaki and Kaede, you have to condemn this sweet person to death while everyone else desperately tries to stop you. In fact, the final battle isn't even ''against'' Gonta; it's Kaito, desperately trying to protect his friend. Needless to say, ''everyone'' hates Kokichi for setting this up- most likely [[MyGodWhatHaveIDone including Kokichi himself]].]]
* ''VisualNovel/DokiDokiLiteratureClub'' is based on introducing cute characters you're supposedly trying to get to date and then [[DisguisedHorrorStory turning into]] horror/tragedy and having bad things happen to them. In the first and biggest instance, your cheerful childhood friend is revealed to be severely depressed, after which you are forced to choose how to respond to her AnguishedDeclarationOfLove. Then you find her dead by suicide, and the game blames you for making the wrong choice, [[MortonsFork whichever one it was]]. And the PlayerCharacter agonises it's not just some video game where you can start over and try again... [[TricksterGame and it turns out you really can't]], but instead have to follow along as the game gets increasingly more freaky and starts targeting the remaining characters.
* ''VisualNovel/FateStayNight'':
** In the ''Heaven's Feel'' route, you're forced to select the choice that kills Saber in order to obtain the True End. This is because choosing to let Saber live has fatal consequences for Rin, who, as a result of Saber's timely intervention, gets absorbed by Sakura. She then proceeds to inflict a [[RapeAsBackstory re-enactment of her experiences in the Matou household]] on Rin, and the utter horror of the scene is compounded when Sakura lets Shirou know in an arrestingly deadpan manner that Rin was a virgin, and that she's "already crying on her first day."
** If that wasn't already bad enough, the True End route also has Ilya sacrifice herself; this is non-negotiable on your first play, and the worst part of it all? That innocent little jingle of hers plays as she does so, increasing the tear-inducing factor of the scene by over nine thousand. Worse than this, when you ''do'' get the choice, choosing to prevent Ilya from sacrificing herself leads to the [[DownerEnding Normal end]], which apart from being exceptionally depressing doesn't mention Ilya ''at all'', implying that she probably returned to her castle to live the rest of her (short) life alone, since Shirou is dead and Sakura is far too traumatised and depressed to possibly look after Ilya.
* ''VisualNovel/KatawaShoujo'': Basically every bad ending is this, and the game really chews out the [[WhatTheHellPlayer player for it more than Hisao]].
** In particular, the bad end in [[spoiler:Shizune]]'s route. [[spoiler:She tells Hisao that she's always had to be the best in anything and everything she does, causing her to be selfish all the time. She feels that this flaw of hers is causing her to push away him and Misha, so she breaks up with him, thinking it's entirely her fault it's come to this. The last thing you see is her sitting on the steps, completely friendless, [[CallBack with the stuffed cat you won for her in Act 1]] hanging out of her bag.]] How do you get this ending? [[spoiler:By cheating on her with Misha.]] And for worse? [[spoiler:After the cheating deed is done, we learn Misha's ''painful'' reasons to ask Hisao for sexual comfort. She came to him because she's in love with ''Shizune'', has been for a long time, and was completely ''[[SexForSolace desperate]]''. Doing the act with Misha causes the two of you to distance yourselves from Shizune out of guilt, which is why Shizune thinks she's pushing you both away. In other words, you cause her to not only lose her only two real friends in the world, but you lead her to think it's all her fault. YouBastard.]]
** Much worse is [[ShrinkingViolet Hanako]]'s Bad Ending: [[spoiler:Hanako, in a shocking [[RageBreakingPoint explosive fit of rage]], screams at Hisao for establishing their relationship purely on [[DontYouDarePityMe pity]] and not viewing her as an equal. Her pure anger seems to be aimed not at Hisao, but at ''you, the player'', because Hanako being TheWoobie is likely why the player chose to pursue her in the first place]]. Her Neutral Ending isn't much better; [[spoiler:after eating some food together and playing chess ([[CallBack like they do in her Act 1 ending]]), Hanako and Hisao remain on good terms, but after all the time the player has spent trying to help her, their relationship has gone [[ShaggyDogStory nowhere]]. Hanako even lampshades this]].
** Rin's Neutral Ending could count even more than her Bad Ending, [[spoiler:because you get it by failing to connect with her in the way she wanted you to. She gets an art scholarship in Tokyo, which means leaving Hisao. She asks if he hates her, he replies in the negative, and she hugs him (as well as she can), answering that it would be easier if he did. Hisao tells her it's hard to hate her when she's hugging him like that, to which she just answers "I can't hug anyone, Hisao. I'm a bad person like that. That's why I have to go." before walking out of his life]].
* ''VisualNovel/MuvLuvAlternative'' is chock-full of these, and when you start feeling like you've gotten used to them, they just blindside you anyway. It probably really starts all going to hell when instructor Jinguuji dies horrifically, and it just keeps getting worse and worse from there.
** Shortly after that, Takeru panics and runs back to his original world and in so doing indirectly brings about Jinguuji's horrific death in that timeline *again* and it gets worse still as everyone who ever cared for him starts to forget him, even Sumika who loves him dearly. Then Sumika gets in a terrible accident that very nearly kills her, again indirectly caused by Takeru fleeing to the Extra world.
** Following those events Takeru [[spoiler: essentially gives up and wants to die but Yuuko helps him get back to the alternative world, giving him hope he can fix everything again if he goes back.]] When he arrives there he learns the true fate of [[spoiler: Sumika in the alternative world which was incomprehensibly horrific. but she was still alive as a brain in a jar, until recently. now her soul got ported into a quantum computer (killing the brain in the process) and her existence now forms the core of the last hope of human victory over the BETA. Takeru just has to get her back into... working order. Not an easy task with her mind so utterly broken by the trauma she experienced followed by 3 years of living as just a brain]]
** Things start to look up a little and Takeru's first big mission to [[spoiler: Assault Sadogashima's hive in a huge offensive]] goes very promising, but in the end [[spoiler: his captain, Isumi, has to sacrifice herself to save the day.]]
** After the aftermath of that big mess settles down [[spoiler: Sumika seems to be doing very well but unexpectedly rejects Takeru when he confesses his love for her. She also convinced Yuuko to remove him from his unit and stop him from piloting a TSF ever again, dashing his hopes on saving the world and undoing the damage he caused in the Extra world.]]
** [[spoiler:Sumika's true motivations are revealed in the aftermath of the [[FinalBattle Operation Cherry Blossom]], wherein Takeru has already lost the entirety of his squad save for Kasumi. It turns out that Sumika had served as an UnwittingPawn for the BETA throughout the story, and her longing for Takeru was a key reason behind him landing in the world of ''Unlimited'' and ''Alternative''. Sumika originally wanted to undertake the entirety of Operation Cherry Blossom ''by herself'', and had no intention of making it out of there alive. With her death, Takeru ceases to be a Causality Conductor, and will return to a new version of his original world, leaving behind the world of ''Alternative'' forever.]]
* ''VisualNovel/{{Planetarian}}'': It comes to punch you in the eye when you're already attached to Yumemi/Reverie.
* ''VisualNovel/TrueLoveJunaiMonogatari'' gives us [[spoiler:[[GirlNextDoor Mikae]] potentially [[WhatTheHellHero snapping on the MC]] in [[TheOjou Remi]]'s path, her reason being that she believes he's kept her hanging on instead of straightforwardly saying he prefers Remi]]. What makes this a player punch? [[spoiler:The incident happens during a date with Mikae. ''One that takes place during her birthday''.]] And for worse, [[spoiler:if you ''do'' go for Mikae's path instead and the date itself goes smoothly... you get to see how the girl has placed ''all'' of her romantic illusions on the MC (including turning down the RomanticFalseLead several times, due to her strong belief that she still has a shot at the MC's heart), and what the apparently innocuous "birthday date" ''actually'' means for her (the chance to get together with a guy [[ChildhoodFriendRomance whom she has liked since they were kids]] and be able to start an adult, long-lasting relationship with him)]]. YEOWCH.
* ''VisualNovel/VirtuesLastReward'':
** If you betray Luna in the third round on her route, not only does this lead to a bad end, Zero III unexpectedly shows up to chew Sigma (and by extension the player) out for it.
** In Quark's route, if Sigma gives into Dio's blackmail and allies with him, Dio betrays him, ensuring his own escape and also leaving Sigma minutes from death.
* ''VisualNovel/YourTurnToDie'': In the second Main Game, voting for [[spoiler:[[ShrinkingViolet Kanna Kizuchi]] (an innocent, emotionally traumatized child)'s death nets you a terrible surprise at the end of the chapter -- [[WildCard Sou Hiyori]] becomes so enraged by your decision to kill his MoralityChain that he activates a twisted, hateful AI of the protagonist's late best friend. The chapter ends with it calling you a murderer and the protagonist forgetting that her best friend even existed]].
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