According to writer and director David Swift, after looking at 362 girls for the part of Pollyanna, they still did not have anyone to play the part. One day, producer Walt Disney's wife Lilly went shopping with Disney studio head Bill Anderson's wife while they were in London, England, on business. The two ladies saw Hayley Mills in Tiger Bay (1959) and thought she was perfect for the role of Pollyanna. The two men didn't listen to them, but they were so persistent that the men finally agreed to watch the movie and immediately decided to cast Hayley.
When this movie performed below expectations at the box office, producer Walt Disney put out his theory for the movie's disappointing performance: "I think the picture would have done better with a different title. Girls and women went to it, but men tended to stay away because it sounded sweet and sticky."
Writer and director David Swift wanted to trim this movie by about twenty minutes and rearrange some scenes (most notably the acquisition of the doll in the town bazaar sequence). But producer Walt Disney, who had fallen in love with this movie by watching the dailies, would not allow it, and Swift did not have final-cut privileges.
Roy O. Disney, studio business head and brother to producer Walt Disney, issued thousands of "Pollyanna photo locket necklaces" as a promotional item containing the famous quote attributed to Abraham Lincoln in this movie. Discovering the necklace in a gift shop while on vacation with his family, writer and director David Swift called the studio to have the item recalled immediately. It turned out that Lincoln had never said, "When you look for the bad in mankind expecting to find it, you surely will." Swift had simply made it up.
This marks the first of six movies Hayley Mills made during her five-year contract with Walt Disney Studios.
David Swift: The fireman shown shooing the small boy off of a ladder after the boiler accident at the Harrington House Orphanage.