In 2017, Pruitt was awarded the Buddy Holly Prize from the Songwriters Hall of Fame and signed with Round Hill Records. Her EP,
OurVinyl Live Session EP was released in March 2018. She was named by
Rolling Stone as one of 10 new country artists you need to know and by
NPR as one of the 20 artists to watch, highlighting Pruitt as someone who "possesses a soaring, nuanced and expressive voice, and writes with devastating honesty". On September 13, 2019, Pruitt released "Expectations", the title track from her full-length debut. Additional singles from this project were subsequently released: "Loving Her" on October 21, 2019, and "Out of the Blue" on November 15, 2019. On February 21, 2020, Pruitt's debut album,
Expectations, was released by Rounder Records. She earned a nomination for Emerging Act of the Year at the 2020
Americana Music Honors & Awards. In the same year, she duetted with Canadian singer-songwriter
Donovan Woods on "She Waits for Me to Come Back Down", a track from his album
Without People. In 2021 the artist was inter alia part of the
Newport Folk Festival in July. On March 18, 2022, Pruitt recorded an episode of The Caverns Sessions (previously known as
Bluegrass Underground), which aired nationally on
PBS on October 15, 2022. == Artistry ==