Recorded at the Butcher Shoppe in Nashville, the album was produced by Sturgill Simpson and was released on August 2, 2019, jointly through Childers' own independent label Hickman Holler Records and major label RCA.

[3] The album received a Metacritic rating of 85 based on six reviews, indicating universal acclaim.

[9] Following the critical success of his breakthrough 2017 album Purgatory, Childers signed an exclusive licensing deal with major label RCA Records and announced his follow up album, named Country Squire, on May 16, 2019.

[10] As part of his deal with RCA, Childers would own the copyright through his own Hickman Holler Records and have creative control.

"[14] The penultimate track of the album, "All Your'n", was nominated for Best Solo Country Performance at the 2019 Grammy Awards, but lost out to Willie Nelson and his song "Ride Me Back Home".