With the name paying homage to The Highwaymen, the Highwomen were originally intended to leave the fourth spot in their line-up vacant to allow other female collaborators to join them, with Chely Wright, Courtney Marie Andrews, Margo Price, Janelle Monáe and Sheryl Crow mentioned as potential guests.

[9] The song was promoted by country singer Dierks Bentley, who released a comedic reading of the lyrics to his YouTube Channel, which received praise from Carlile and Morris.

[11] In July 2019, the Highwomen performed their first ever full live set at the 60th annual Newport Folk Festival, previewing songs from their upcoming album including "If She Ever Leaves Me", written by Shires, her husband Jason Isbell and Chris Thompkins.

Other songs performed included "My Only Child", an ode to "suburban moms" performed by Hemby, who wrote the track with Shires and Miranda Lambert; "Loose Change", a nod to '70s country written by Morris, Daniel Layus of Augustana, and Maggie Chapman, featuring Morris on lead vocals; and "Cocktail and a Song", which was written solely by Shires in honor of her father.

Carlile later invited the rest of the Highwomen to join her during her headlining set, where, as they originally intended, the group performed alongside other female artists including Amy Ray, Courtney Marie Andrews, Dolly Parton, Jade Bird, Judy Collins, Linda Perry, Lucy Dacus, Our Native Daughters, Sheryl Crow, The First Ladies of Bluegrass, and Yola Carter.

[4] Songwriters included the aforementioned Jimmy Webb, Rodney Clawson, Maggie Chapman, Lori McKenna, Jason Isbell, Peter Levin, Miranda Lambert, Ray LaMontagne, among many others.

They also performed "Coal Miner's Daughter" during a tribute show on CMT following the death of Loretta Lynn, with Brittney Spencer standing in for Morris.