It had been almost a year since Princess Twilight Sparkle became the new leader of Equestria as her first Nightmare Night since ascending to the throne draws near a new face appears in Ponyville who to some is giving off a dark vibe, to others a mysterious yet friendly vibe. Regardless, this new citizen reveals himself to be King Jack O' Lantern, the basis for the Headless Horse story. However, Jack's appearance sparks fear in the festival goers.

Despite the chaos he caused Jack explains that he is not there for any ill intentions or malice but rather to announce that he is moving into Princess Celestia and Princess Luna's old castle in Everfree which unfortunately for him causes more panic. Time will tell if King Jack's words of only being benevolent are true or a fabricated lie.