The special took three years to complete; the script was written between July and September 2015, with the July-written portions being done whilst on a Croatian holiday. The animation itself was produced in-and-out during Milan's Grade 11 and 12 years of high school, with the majority of the work being completed in July and August 2017.
The decision to bring on Phillipa Alexander as Calley was one made towards the final stages of animation on the special; the original actress had been fired, and Milan was unable to find a replacement that would fit. Seeing the opportunity for a guest spot on the special, he contacted Phillipa, who agreed to record for the special after a deal was made.
The special originally planned to be produced as a direct-to-video release, but was released to YouTube first instead; the release was bolstered by a week of advertising and a special two-hour live marathon entitled "The Tillie to the Rescue Feast of Fun", in which a workprint of the special (due to last minute technical problems) was screened; it became the highest-viewed MilanToon Channel stream to date, with a record viewer peak of 156.
The "Nothing Can Stop Us Now" musical sequence was done during the final stages of production; the scene originally contained narration, but it was decided that a cover of the song would be better suited. Only the "I think I can, I THINK I can" line was retained. There was also another Tillie line was cut from the scene: "Make way for the Little Engine Express!", originally written in for the "Run-Over" shot of the sequence.