[8] As a teenager she lived overseas, where she spent much of her time listening to her brother's records of Neil Young and Bob Dylan.

After high school she decided not to attend post-secondary education, instead opting to play local clubs to pay the bills.

Rolling Stone declared her one of year's most promising new acts and Blender said that Failer's songs possessed "an indefinable pull that makes you love the characters they describe, no matter how fucked up they are."

The New York Times praised Edwards as a writer whose songs can "pare situations down to a few dozen words while they push country-rock towards its primal impulses of thump and twang."

It was described by the San Francisco Bay Guardian as "her finest album to date",[11] and was a shortlisted nominee for the 2008 Polaris Music Prize.

[12] In contrast with 2005's Back to Me, on which Edwards relied on her working band, Asking for Flowers predominantly features session musicians.

[16] In 2005, Edwards lent her vocals to the duet "The Plan", recorded with Matt Mays and El Torpedo for their self-titled album.

[18] In 2007, Edwards worked with John Doe, of the punk rock band X, on his solo album A Year in the Wilderness.

"Soft Place to Land", one of two songs on Edwards' Voyageur album co-written with The Long Winters frontman John Roderick, won the 2012 SOCAN Echo Songwriting Prize.

[26] Edwards stepped back from the music scene in 2014, launching a coffee house in Stittsville called Quitters along with Rick Tremblay (who was her manager when she worked in a downtown Starbucks in the 1990s).

[29] In August 2019, following the suicide of American singer-songwriter Neal Casal, Edwards opened up on Twitter about the struggle with depression that led her to take time away from her music career.