Tortall Universe/Tear Jerker

The Lioness Quartet

• Tears were shed for the deaths of Thom, Faithful, and Liam Ironarm.

The Wild Magic Quartet

• Important and beloved characters often die violently and tragically. Rikash's death scene made this Troper cry like a baby.

The Protector of the Small Quartet

• In "Squire", after Crown and Freckle have died, and Kel has buried Freckle next to Crown.

"It's the only bad thing about animals," she told Cleon. "Most don't live as long as we do.
"I know, sweet," Cleon said, kissing first on of her eyelids, then the other. "But think how bleak life would be without them."

The Trickster books

• YMMV but the murders of Elsren and Dunevon, as well as several other little boys during a birthday party are quite possibly some of the most heartwrenching parts of the entire series.
  • Made even worse when it's hammered in that this was probably the most merciful outcome because in order for the revolution to succeed, it's necessary to remove any of the Luarin who might have a claim to the throne, including Elsren, meaning that by having Kyprioth manipulate the regents into orchestrating their deaths, the members of the conspiracy were saved from having to do the dirty work themselves.

The Beka Cooper books

• The spinner next to the prison, made even worse by the fact that it has no way to block out what it hears.
• Tunstall, a very dear friend to Beka from the beginning and a hitherto-unquestionably good guy, betraying her, murdering many people, and attempting to murder a four year old prince, just because if he did, he would be made prime minister in a conspiracy to overthrow the throne, thus making him noble and good enough for Sabine. Both weeping the entire time, he and Beka must fight, during which time he says things like "You're like a daughter to me, don't make me kill you!". In the end, he begs for Beka to kill him, which she won't. She instead arrests him, taking him to his torture and execution with a torn up heart, except he never makes it because he dies of a combination of his wounds and chill on the way there. Completely out of left field, but beautifully written.
  • The knife is twisted when Tunstall's ghost returns briefly, riding on a pigeon. He makes it pretty clear that he knows what he did was wrong and he regrets it, but even if he hadn't died, he would never have had the chance to redeem himself, especially to Sabine.

Beka: Don't blame her. She would have married you had you asked, if she agreed to marry anyone. She adored you, and you betrayed her.
Tunstall: And you settled the bill, or started me along the path to settling it, Cooper. The chill of the night and the weakness from my hurts, that finished it, but you put me on the path to your god. Tell her I love her and beg her forgiveness, Cooper. And I love you and Goodwin. The pair of you have always been my true sisters.

• The description of the funeral of Holborn, Beka's fiance. Even though we never get to see him onscreen, it's still heartbreaking, especially when his family express their sadness that Beka never officially joined them.