- Lady Tremaine goes out of her way to torment Cinderella one last time before she and her daughters leave for the palace by taking her last glass slipper, breaking it, and telling her to clean it up before she leaves.
- Prudence leads Cinderella away from the Prince and orders her to search for Jaq and Gus, essentially leaving Cinderella back where she started. The hopeless look on her face and way she quietly wipes her tears away only makes it more heartbreaking.
- Cinderella's Dark Reprise of "More Than a Dream" when she's about to be shipped out of the kingdom. It's fair to say she's been through hell twice, and at this point not even Cinderella has anymore optimism left.
- Anastasia's whole character arc is heartbreaking because she's getting all this love and attention—possibly the only real love and affection she's ever had—for something she didn't do. Everyone in her life either thinks she's something she's not, is emotionally abusive, or has been made out to be her enemy.
- Anatasia's protest "But I want someone to love me for me!" when she ruins her wedding to the Prince. Would she have been so desperate to catch a boy's eye if her own mother had truly loved her?
- Hell, her Heel Realization begins when Cinderella asks her if being the Prince would really make her happy, and if she even loves him. She realizes that no, this won't make her happy - and her mother doesn't care.
- Not easy to realize in the moment, but that Drizella and Anastasia are also abuse victims. After Cinderella leaves, their mother treats them the way she treated Cinderella. They're supposed to deserve it because they bullied Cinderella, but Anastasia's plot proves the girls only act the way they do because they weren't taught better and their mother is the only role model they've ever had.
Tear Jerker / Cinderella III: A Twist in Time