Thomas and The Magic Riddle is an upcoming Thomas & Friends/Yoram Gross Crossover film to be created by 76859Thomas. It will appear on Google Drive in the near future.
Cindy, lives with her widowed stepmother and two stepsisters, Bertha and Ertha. Cindy is forced to do all of the housework and is effectively a servant. The widow hates Cindy because her late Grandfather died and hid his will, which the widow knows passes all the family inheritance to Cindy. The widow purposely keeps Cindy busy so that she won't find the will, giving the widow time to find it first.
A young man named Phillippe, who is their neighbour, returns from his studies and is enchanted by Cindy. The widow, however, wants him to marry Bertha.
One night, Cindy falls asleep before finishing her chores. Unknown to her, an old lady sneaks into the house and finishes her chores for her. Ertha encounters the old lady, who reveals that she is Cindy's Grandmother. Ertha agrees to keep Grandmother's visit a secret. The same thing happens the following night, but the widow wakes up and chases Cindy's Grandmother out of the house. Ertha, who witnessed everything, tells Cindy about Grandmother's visit.
The widow asks her magic mirror for advice, and it shows her a salesman disguise. The widow visits Grandmother's house in the woods, and tricks the old lady, who is sent to the Castle of a Hundred Doors, from which there is no escape.
Cindy, dressed in a red riding hood, tries to find her way to Grandmother's house. On the way, Cindy meets a wolf who advises her to walk slowly to avoid danger. When Cindy finally arrives at the house, she is shocked when her "Grandmother" turns out to be the wolf. After Cindy runs away in fear, the wolf removes its mask, revealing that it was the widow.
Cindy sits by a lake, telling her hopes to an ugly duckling, unaware that Phillippe is listening. Phillippe eventually reveals himself and gives her a ring as a token. Later, Bertha scares away their farm's pigs and blames Cindy. Cindy runs back to Grandmother's house, and there she discovers seven wooden dwarfs and the wooden puppet Pinocchio. They come alive when she kisses them, and they tell her that widow took Grandmother away.
The widow decides to lure Cindy back to the house by holding a ball. Cindy learns about the ball and decides to go, as it is a chance to see Phillippe again. The dwarfs make Cindy a white dress, Pinocchio lets her borrow his shoes, and they create a swan-shaped sleigh, as well as a crown and mask out of snow. They warn her that the mask will melt at midnight, so she has to leave before then.
At the ball, the widow keeps an eye out for Cindy. Phillippe is at first forced to dance with Bertha, but when Cindy arrives, he quickly turns his attention to her. Ertha has her own romance when she dances with Pinocchio. When the clock strikes 12, Cindy's disguise melts away and she is forced to run away, with her friends the dwarfs and Pinocchio quickly following. When the widow mocks Ertha for wanting to find Pinocchio, Ertha retaliates by telling Phillippe that Cindy can be found at Grandmother's house. He heads out to find her.
The widow asks her magic mirror for help, and it shows her a disguise: a pointed hat, a nose that looks like Pinocchio's and an apple. The widow arrives at Grandmother's house in the disguise, claiming to be Pinocchio's mother. The widow hypnotises Cindy to fall asleep, and in the commotion the widow falls in a well.
The seven dwarfs, Phillippe and Pinocchio all end up hearing cries for help at the Castle of a Hundred Doors. When Pinocchio enters, one of his shoes is caught on a nail and starts to unravel. After some time Grandmother is found everyone is able to group up, and follow the trail left by Pinocchio's shoe.
When they arrive back at the cottage, Cindy is woken up. Grandmother tells her that Grandfather left her everything in his will, and that the answer is hidden in his magic riddle, a poem which ends with: "Only Pinocchio knows". It turns out that the will is inside Pinocchio's nose. Grandmother reads the will, confirming that all of Grandfather's possessions go to Cindy.
Cindy and Phillippe's wedding is held at what used to be the widow's house. After the celebrations, the dwarfs turn back into wood. But when Ertha kisses Pinocchio, he comes back to life to be with her.
- This film reveals that Cindy is Cool McCool's niece.