Rolling Stone described her music as "a new spin on West Coast folk-rock, with classical tendencies, electric guitars, jazz-school chord changes and alt-rock strut all living under the same roof".

[10][7] In 2017, Cunningham joined the cast of American Public Media's show Live from Here, presented by Chris Thile, of whom she became a frequent collaborator.

[4] In 2020, Cunningham released her third extended play (EP), Wednesday, covering songs by Tom Waits, Radiohead, John Mayer and the Beatles.

NPR music contributor Jewly Hight states that Madison was an "audacious guide, steering us toward exploration with the shrewd parts she played on three different guitars over the course of four songs".

Consequence's editorial coordinator Paolo Ragusa writes about it: "With each song on Revealer, Cunningham is proving that she can satisfy and surprise her audience all at once, and it’s one of the most delightful albums released so far in 2022.