Taylor Swift made her debut as a film director with All Too Well: The Short Film, which premiered on November 12, 2021, at the AMC Lincoln Square 13 theater in New York City and was released on YouTube the same evening. Swift wrote and directed the film, which runs about fifteen minutes and is set to the ten minute version of her song "All Too Well," released that day on Red (Taylor's Version), the second album in the series of rerecordings told in Battle of Masters, after Fearless (Taylor's Version) in April 2021. The series was her plan to own new recordings of her first six albums after their original masters were sold in 2019.

The film stars Sadie Sink and Dylan O'Brien as a young couple whose relationship falls apart, and Swift appears in a cameo as an older version of Sink's character, a writer looking back on the story. At the premiere, after the screening ended, Swift performed the full ten minute song live on a red guitar for the audience.

The original version of "All Too Well" had appeared on Red in 2012 and became a fan favorite without ever being released as a single. The extended version restored lyrics written for the song years earlier.

The short film was later shown at film festivals, including the Tribeca Festival and the Toronto International Film Festival in 2022, where Swift spoke about her approach to writing and directing. At the 65th Grammy Awards in February 2023, it won Best Music Video, with Swift credited as director, after winning Video of the Year at the 2022 MTV Video Music Awards.

Swift had directed or codirected several of her earlier music videos, including "The Man" in 2020, and she went on to write and direct the video for Anti-Hero in 2022. In December 2022, Searchlight Pictures announced that Swift had written an original screenplay and would make her feature film directing debut with the studio. The short film marked the point at which directing became part of her public work, alongside the songwriting that began with her first song at age 12.