From 2010 to 2011, Andrews was an auxiliary member of Jimmy Eat World, appearing on their 2010 studio album Invented and acting as their keyboardist and backing vocalist on the subsequent tour.

In September 2009, Jim Adkins of the band Jimmy Eat World asked Andrews to sing with him on a live cover of Wilco and Feist's song "You and I".

She subsequently joined them on stage to perform during the album's release and full 2010–2011 tours, acting as their keyboardist and backing vocalist.

It was while living in Belgium for four months playing guitar and singing with Belgian star Milow that the songs for Honest Life, Andrews' fifth studio album, started taking shape.

The album was produced entirely by Andrews at Litho Studios in Seattle with audio engineer Floyd Reitsma and was released on August 19, 2016, in North America by Mama Bird Recording Co. and on January 20, 2017, in the UK and Europe by Loose.

Produced by Mark Howard (Lucinda Williams, Bob Dylan, Emmylou Harris, Tom Waits), the album was recorded over eight days at a rented house-turned-studio in Los Angeles, California.

In addition to Andrews on vocals and electric and acoustic guitar, the album features Dillon Warnek (electric guitar), Daniel Walter (organ, Wurlitzer, accordion), Charles Wicklander (piano, Wurlitzer), William Mapp (drums, percussion), Alex Sabel (bass) and C.C.

May Your Kindness Remain received critical acclaim for its release in the United States from Rolling Stone, NPR Music, Chicago Tribune, American Songwriter, WXPN The Key, Bluegrass Situation and more.

Of the single and Andrews, Fader declares "Kindness of Strangers' rules...incredible cut...what a voice she has – it always lifts me up"[15] and Paste magazine recounts that the album is "a rare blend of power and feeling that can bring you to your knees".

The Daily Telegraph called the album "another absolute beauty, a set of nuanced, compassionate portraits and vignettes of good people in difficult circumstances".

[23] She later performed on air at the Americana Music and Honors awards ceremony on September 13, 2018, at the legendary Ryman Auditorium in Nashville, Tennessee.

[30] Rolling Stone described the single "It Must Be Someone Else's Fault" as bringing "to mind classic Bob Dylan and Joni Mitchell, but Andrews' bell-clear voice and fearless message of introspection are unmistakably her own".

[36] In partnership with Sam Evian, a producer who has previously worked with Big Thief and Cassandra Jenkins, Andrews was able to expand her aural palate and transition into a new sonic world.

Pitchfork asserts that "the smooth, radiant production doesn't amount to commercial pandering: it's assured, exploratory, and warm music that mirrors Andrews' newly opened heart.

[38] These themes stem from the timing of the writing, as the songs were penned during the global COVID-19 pandemic and on the heels of the end of a longtime relationship.