Pinegrove had risen to fame on the heels of its sophomore record, Cardinal, released on independent label Run for Cover.

The group, fronted by singer-songwriter Evan Stephens Hall, spent their early years performing at DIY shows and self-releasing their music.

[5] Skylight was released on Bandcamp on September 28, 2018, with profits initially going to various charities, including Musicares, the American Foundation for Suicide Prevention, and the Voting Rights Project.

Pinegrove self-released Skylight, and parted ways with Run for Cover Records, which had initially planned to release the album prior to Hall's announcement.

Corcoran praised the album as lyrically dense, commenting, "Skylight showcases Pinegrove's growth as musicians and the significant steps they’ve taken to hone their sound.

"[1] Uproxx's Philip Cosores considered it a more mature offering than its predecessor, while noting that "it's a record that’s inherent strength could have easily catapulted the band to the next level of their career had the circumstances surrounding it been different.