The tour was in support of her sixth studio album Cry Pretty (2018), and began on May 1, 2019, in Greensboro, North Carolina and concluded on October 31, 2019, in Detroit, Michigan, playing 60 shows.

[2] On March 4, 2019, Underwood announced UK dates revolving around an appearance at the Glastonbury Festival supported by The Shires.

[4] Bob Mehr of Commercial Appeal applauded the show's pyrotechnics, but highlighted Underwood's voice, writing, "Despite all the showmanship, the real essence of Underwood — going all the way back to her breakthrough on American Idol nearly 15 years ago — is her voice, a uniquely thunderous mezzo soprano that has defined a generation of hits, from the opening "Southbound" to the concert capper "Love Wins".

"[5] Billy Dukes of Taste of Country wagered that the show might garner Underwood the CMA Entertainer of the Year award, writing, "The definition of "hit" is clearly changing.

She uses no backing track; it's just her, a nine-piece band (including one female background singer) and those propulsive pipes booming from the PA."[8] This setlist is representative of the show on May 1, 2019, in Greensboro.