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The Sun Trail
- In Sign of the Moon, Jayfeather leaves the past thinking that things will be better off now. Reading the beginning of The Sun Trail and seeing just how bad things are for the Tribe is hard, to say the least.
- Fluttering Bird's death. We may not have known her very well, but she was just a kit with her whole life ahead of her. It gets worse when Quiet Rain and Gray Wing start blaming themselves. Then we have to experience it all over again when he see the enthusiasm drain out of Clear Sky and Jagged Peak.
- When Gray Wing sets out to find Jagged Peak. It's not enough for him to be leaving the only home he's ever known. The ice bridge he's crossing collapses under him, leaving his mother Quiet Rain unsure whether he's alive or dead. He tries to tell her that he's alive, but there's no way of knowing if she heard him.
- When Bright Stream dies. Clear Sky thought that he would be with her in his new home, but he finally realizes that he shouldn't have been so obsessed with himself. Also, the way Gray Wing blames himself, and thinks that Clear Sky hates him, is depressing as well.
- Shaded Moss's death and funeral. He died just a short walk away from the new territories. The cats sharing their memories of him makes it even worse, and then Clear Sky has to add in Bright Stream...
- On the first time reading through the book, Gray Wing accidentally killing Fox is a Tear Jerker because of the despair Gray Wing feels over killing another cat. The second time around it becomes even worse, because now you know that Fox isn't just a random jerk. From the bonus scene, you know his hopes and dreams, and how absolutely crushing this will be for Petal. Ouch.
- Turtle Tail's departure. Gray Wing doesn't even understand that she loves him, and can't say the words she needs to hear. Storm getting together with Clear Sky afterwards hammers in that Gray Wing made the wrong choice.
- Gray Wing telling Clear Sky to call after Storm. Clear Sky clearly wants to, but he can't or he'll betray his principles. It just shows how broken everyone is.
- Storm's death. With her last words, she asks Gray Wing to tell Clear Sky that she's sorry. It's like Bright Stream all over again, but even worse.
- Rainswept Flower's nightmares after her father dies. It hurts.
- Moon Shadow's death and subsequent funeral.
- When Clear Sky kills Misty, only to realize that she was just protecting her kits.
- Bumble's death. Holy crap, Bumble's death.
- Clear Sky bullying Jagged Peak just when the latter was minding his own business. When called out by Gray Wing, Clear Sky tries to apologize only for Jagged Peak to call him a terrible brother.
The First Battle
- Thunder and Lightning Tail finding Turtle Tail dead. The way Lightning Tail pleads for her to get up is heartbreaking.
- Turtle Tail's death in general, really. After finally becoming mates with Gray Wing and making him happy, being one of Thunder's few allies at first and the scene where they watch Wind Runner's kits being born (which Thunder sadly recalls upon finding Turtle Tail's body)... Turtle Tail's death is enough to rip anyone's heart out.
- Emberkit's death. Wind Runner is completely consumed by grief, and when Gray Wing tries (poorly) to comfort her, she screams at him that he's as bad as Clear Sky and tells him that when he loses someone, she'll throw his words about them "being in a better place" right back in his face. It gets worse when the Moor Group finds out that Turtle Tail is dead and Wind Runner regrets what she said.
- All the cats who died over the arc briefly coming back at the end of the book to deliver a message, including the those who died in the battle, Turtle Tail, and Emberkit. Even though you know it's coming, it brings up tears when all these cats reunite with their living friends and family.
The Blazing Star
- Acorn Fur leaving the Moor Group because she knows that if she goes back there, she'll keep expecting to see her parents but it won't happen. It's even worse with how heartbroken Lightning Tail is.
- Thunder having to exile Star Flower after she betrays him, all the while wondering if what they had was ever real.
But while River Ripple padded away, Thunder couldn't tear his gaze from the spot where he had last seen Star Flower.
I'm not so sure there will be others...
- Petal, the one cat who had supported Clear Sky no matter what, dying to save her kits. Especially with Clear Sky realizing how much she meant to him.
- Gray Wing's slow breakdown after Sparrow Fur leaves the moor and gets injured.
- Wind Runner leaving the moor after she loses another kit.
A Forest Divided
- Thunder and Clear Sky arguing yet again when Clear Sky takes Star Flower as a mate when Thunder would not forgive her. But this time, Thunder makes his own camp in retaliation.
- Quiet Rain's death, surrounded by her sons.
Path of Stars
- Gray Wing's death, with his friends and family saying goodbye.