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1* Keris being united with her grandmother at the end of ''The Slaughterer's Quest.''
2* Cloud Wolf [[spoiler: being absorbed into the Mother Storm]] while Twig tries desperately to keep him alive.
3* That poor banderbear in ''Beyond the Deepwoods''. Twig's finally made a friend who doesn't hate or bully him, only to be devoured by those damn wig-wigs.
4-->Twig wiped his eyes and looked down. The wig-wigs had gone. And of the banderbear, there wasn't a trace to be seen, not a bone, not a tooth or claw, not a single scrap of mossy fur. From far away there came the forlorn yodelling call of a distant banderbear. Time after time its heartrending cry echoed through the trees.\
5Twig held the tooth around his neck tightly in his hand. He sniffed. "It can't answer you now," he whispered tearfully. "Or ever again."
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7* Maugin in the Stone Pilot, upon being captured by the slaver and realizing she has missed her ceremony and will never turn termagent, meaning she will always be an outsider in her own home. Even after Quint rescues her she doesn't really pull out of her misery until she takes up Ramrock's hood.
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9* Twig accidentally finding his way [[spoiler: back home via a woodtroll path]] in ''Midnight over Sanctaphrax'', only to walk in on [[spoiler: his father's, Tuntum's, funeral]]. Made even more tear-worthy when you realize that [[spoiler: he's now lost both fathers in one fell swoop]].
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11* At the end of Midnight Over Sancataphrax, Cowlquape plans for New Sanctaphrax to be a fresh start and a brighter future for the Edge. The very next book reveals all his plans fell apart before they really got going thanks to Stone Sickness, he was betrayed, and things in Undertown are worse than ever.
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13* Twig losing his entire hand-picked crew on his attempt to return to Riverrise for the second time. And then, when the caterbird finally flies him all the way there at the end of his natural life.. Maugin is shot seconds before he lands and Goom and Woodfish have both wandered off years previously.
14** Making it worse, Stormchaser starts two years after Beyond the Deepwoods. In Stormchaser Twig loses his father again, and in Midnight he loses his crew (who are never fully reunited again). Those two years between Deepwoods and Stormchaser are the literally the only time in Twigs life that he isn't separated from any of his family, and even then he never got back to the woodtroll village in that time.
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16* In general, the rapid expiry date of PlotArmour in the series makes so many moments HarsherInHindsight. The Rook trilogy's characters are the only ones who actually get to keep their happy ending, and even then [[spoiler:Rook himself becomes one of the immortals, mitigated only by the fact that he'd left the Free Glades after the deaths of his friends, not expecting to return alive.]]
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