Windy City

She picked the ten songs with the producer Buddy Cannon. They include the Osborne Brothers' Windy City and It's Goodbye and So Long to You, Roger Miller's River in the Rain, John Hartford's Gentle on My Mind, Willie Nelson's I Never Cared for You and the Cindy Walker and Eddy Arnold song You Don't Know Me. The sessions took place in 2013 and 2016 at eight Nashville studios, among them Blackbird, Ocean Way and Sound Emporium. Krauss told Garden & Gun in 2017 that when she is drawn to a song, "it's the pictures I see".

It opened at number one on the country and Americana charts in the US and UK and at number 9 on the Billboard 200, with 38,000 units in its first week. Mark Deming of AllMusic called it "a richly satisfying experience". Stephen M. Deusner of Pitchfork wrote that the easy listening criticism had dogged her for more than twenty years and found her Gentle on My Mind "technically sharp but emotionally blunted". He praised her closing You Don't Know Me. It earned two Grammy nominations, for Best Country Solo Performance and Best American Roots Performance.