A single, "Another December", was released on YouTube November 29, 2018. The song was focuses on Hart's mother and the accompanying video features photos of her with family interspersed among present-day footage of Hart walking through Montreal. The video was a preview for a new EP; the title track "Dreaming Time Again" was released January 16, 2019 with an accompanying video filmed in Havana, Cuba featuring Hart's teenage son, Rain. The EP was released in the spring that year in association with Warner Brothers Music Canada, and Hart set out on a cross-country tour, beginning in St. John's, Newfoundland on May 31.