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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:
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  1. In general, Anastasia seems a bit less of a jerkass 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).

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