The Highwomen had 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.

[1] The group made their live debut on April 1, 2019, at Loretta Lynn's 87th birthday concert, held at the Bridgestone Arena in Nashville.

There, Natalie Hemby was officially revealed as the final member and the quartet performed "It Wasn't God Who Made Honky Tonk Angels".

[5] On July 30, the Highwomen appeared on The Tonight Show with Jimmy Fallon, where they performed "Redesigning Women" and "Crowded Table".

[6] 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.

The song was re-written by Carlile and Shires — with Webb's blessing and assistance — as a response song reflecting how women throughout history often sacrifice themselves for a greater good, illustrating this with a Honduran immigrant who dies getting her children over the border (sung by Carlile), a healer executed for witchcraft (Shires), a freedom rider (guest vocals from Yola), and a preacher (Hemby); Sheryl Crow also provided backing vocals.

Rolling Stone said that the song "puts a woman’s experience front and center, with just enough punch to make it smart, self-deprecating, and sarcastic all at once.

[10] "Crowded Table", the fourth track and second single, was written by band members Hemby and Carlile with Lori McKenna.

[10] "If She Ever Leaves Me", the album's sixth track, was written by band member Amanda Shires with her husband Jason Isbell and Chris Thompkins.

The album's tenth track, "Heaven Is a Honky Tonk", was written by members Carlile and Hemby with Ray LaMontagne, and features Sheryl Crow and background vocals by Yola.

[11] Chris Willman from Variety called the album an "instant classic," and went on to say that "the all-star foursome has put together an album full of high comedy and high pathos, zingy group-sings and gut-wreching solo turns, wryness and rue, and harmony co-existing with this strange and nearly forgotten thing called twang.

"[15] Writing for AllMusic, Stephen Thomas Erlewine gave the album four out of five stars and said, "The record's resonance lies in its deep emotions and sense of craft.

His review said, "What’s most impressive about The Highwomen, handsomely produced with Nashville neoclassicist Dave Cobb, is how artfully, and matter-of-factly, it engages social issues.

"[23] In a mixed review for The Guardian, Michael Hann gave the album three out of five stars and said, "Four voices aren’t always stronger than one, and the collegiate nature of the record leaves one yearning for a little more single-mindedness.