- Jerkass Woobie: Trixie. Oh, poor, poor Trixie. While the story is ostensibly a comedy, it's hard not to feel sorry for the poor girl as she endures almost nonstop physical and psychological abuse that she arguably doesn't deserve for a crime that she's arguably not in any way responsible for. While she begins the story as her usual haughty, arrogant self, by the end she's clearly a traumatized wreck, having been physically, psychologically, and emotionally tortured over the course of the last few days. Even at the tail end of her epic Humiliation Conga, instead of being sincere with her, the Princesses cruelly tease her by offering leniency, only to immediately take it away again, laughing in her face. Her following "The Reason You Suck" Speech and Downer Ending makes her buying the Alicorn Amulet and going after Twilight feel totally justified.
...on the other hand...
As bad as the Princesses are, to be fair, they are trying to rehabilitate her, and they do present her with several opportunities to show them that she's learned the error of her ways, or even just acknowledging that she could be a better pony than she is. And yet every time, Trixie switches back to Jerkass mode, throwing all her woobie cred out the window to (figuratively) spit in the Princess' faces, out of spite, stubbornness, and refusal to take any responsibility or feel any guilt for the events that happened in Ponyville. All she has to do to make the torture stop is give some kind of sign, anything, that proves she's willing to atone for what happened. In the end that's exactly what she does, and it seems like everything's gonna end happily...until the Princesses test her one last time. Which she fails, spectacularly, choosing to lay a long, elaborate Humiliation Conga trap for the Princesses instead of doing the chores she volunteered for. Despite how much she suffers as a result of falling victim to her own trap, and despite the Princesses setting her up for temptation, it's also hard not to concede that she brought it entirely on herself.
- Exaggerated in the first nightmare sequence, where Luna presents her normal, jerkass self with the personification of her woobie self, which is about as literal as this trope can get.
- Moral Event Horizon: The Princess' gleeful mistreatment of Trixie is enough to make them seem unsympathetic, for the most part their treatment seems more playful than actively malicious. Then the end of the first day comes. In the middle of a pleasant power fantasy dream, we find out that Luna has entered the dream with Celestia, and is actively twisting it into a nightmare. They give Trixie no relief from her sentence, which they said from the outset will last indefinitely, not even when she sleeps. For some, this is when they officially cross the line into villain territory. No wonder the poor girl breaks down so quickly.
YMMV / The Sun And Moon Are Harsh Mistresses