"Country Squire", a second album under the Hickman Holler label, and Childers' third overall, was released on August 2, 2019, after being announced in May 2019. This album was again produced by Simpson and Ferguson. The video of the lead single from the album "House Fire" was also released on May 16, 2019. "All Your'n," the second single from the album, was nominated for Best Country Solo Performance at the 62nd Annual Grammy Awards.