[2] On August 12, 2022, Sylvan Esso released their fourth studio album, No Rules Sandy, to positive reviews on their Psychic Hotline label.

[3] Lead singer Amelia Meath, who was at the time involved with her trio, Mountain Man, created the vocals to the song called "Play It Right".

The band derived the first part of its name, "sylvan", from a character in an early iOS game titled "Sword and Sworcery".

They made their network television debut on The Tonight Show Starring Jimmy Fallon on July 9, 2014, performing the single "Coffee".

[citation needed] In August 2015, the band also released "Jaime's Song" which was specially recorded for NPR's Radiolab, as a tribute to a story about bipolar disorder.

[16] In late February the group released the single “Die Young” along with a music video and an announcement regarding their new album, titled What Now.

[23] The band covered five songs from What Now with additional instrumentation by Matt Douglas, Ryan Gustafson, Molly Sarlé, Alexandra Sauser-Monnig, Jenn Wasner, and Joe Westerlund.

[24] In the expanded band, Meath and Sanborn were joined by Meg Duffy, Molly Sarlé, Daughter of Swords, Jenn Wasner, Dev Gupta, Adam Schatz, Matt McCaughan, and Joe Westerlund.

Meath performed the track live from the back of a moving pick-up truck for Full Frontal with Samantha Bee.

[28] Free Love’s next single, “Rooftop Dancing,” was released on August 11, 2020 alongside a music video directed by New York photographer and filmmaker Cheryl Dunn.

The project included a video[3] with a 20 minute improvised modular set by Nick (sampling from the album), interviews with music video directors, various art pieces by Nathaniel Russell, an improvised dance by Emma Portner to "Numb", a song dedicated to the band by Jeff Tweedy and a DJ set by Merrill Garbus of Tune-Yards.

[38] A few days later on November 23, Sylvan Esso released their Shaking Out the Numb podcast, a six-episode series centered on the making of Free Love and beyond, made with Rumble Strip producer Erica Heilman.

[40] On May 19, 2022, the band released the single "Sunburn" on streaming services, with album artwork including "Sylvan Esso IIII".

They're sad songs that sound really happy.”[47] The New York Times wrote of the duo's singular style, “Sylvan Esso evades the booming, repetitive overkill of typical electronic dance music.