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WMG / Cinderella II: Dreams Come True

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Disney didn't make a series focused on Cinderella's life as a Princess because the idea was pitched too soon.
Cinderella is a girl who used to have a poor life until she suddenly became a Princess and has to get used to her new role. That's not different from a certain Disney character who later got her own series.
  • It makes more sense when you remember Cinderella was the first of the Disney Princesses to mentor Sofia.

Lady Tremaine believes it was to make her upset that Cinderella encouraged Anastasia to pursue true love.

Chronologically, this movie takes place AFTER Cinderella III: A Twist in Time.
This theory is based on a couple of factors:
  1. In general, Anastasia seems a bit less of a jerkass, and not quite as deep under her mother's influence at the start of this movie than at the start of A Twist in Time. The implied regression between films would be strange and unjustified either way, but it would at least be smaller if this film were to go third instead of second in the timeline.
  2. During their verse of "Perfectly Perfect" in A Twist in Time, the stepsisters lament that they have yet to be invited to a single castle ball; meanwhile, Anastasia attends one at the end of this movie.

And given Cinderella's tendency to easily forgive and the possible interpretation that she does crave some degree of approval from her stepfamily, it doesn't sound too far-fetched that she might grant a pardon to Tremaine and Drizella if they were in fact sentenced to castle servitude as the stinger of A Twist in Time implies (although alternatively, it may be possible they were just dressed as maids to tease them), even if Tremaine would be ungrateful about it (and thus keep her personality as is across all three films).

This movie was retconned by Cinderella III: A Twist in Time.
But of course, there is the opposing theory that the third and final segment could not have come to pass after the events of A Twist in Time
  • Although Cinderella may have wanted to grant a pardon to Lady Tremaine and Drizella, believing further punishment to be pointless, the King may have felt the need to either keep them as servants or have them exiled to protect both her and Anastasia. This would thus prevent Lady Tremaine from getting her hands on Cinderella or Anastasia, or even being able to return to her château and recalculate her plans.
    • Furthermore, even if Lady Tremaine and Drizella were allowed to leave the Palace, Cinderella and the King would doubtless do everything they possibly could to protect Anastasia.
  • In either case, Anastasia would be able to avoid any form of regression at the hands of her mother, and would allow her to find love in the form of the baker far more easily, and grow closer still to Cinderella and the Prince.

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