On March 13, 2014, it was announced that drummer Longineu W. Parsons III left Yellowcard to pursue "other musical interests".

[6] A week later, the group signed a multi-album deal with independent label Razor & Tie, scheduling a new album in the fall.

Razor & Tie owners Cliff Chenfeld and Craig Balsam said that the band "rock the way we like it—with energy, hooks and attitude.

[8] Sessions for Lift a Sail were held at The Casita, and EastWest Studios, with producer Neal Avron.

Avron mixed the recordings, before Ted Jensen mastered the album at Sterling Sound in New York City.

Alternative Press writer Matt Crane said the video "aligns the band with Invisible Children, who work to end the violent reign of Joseph Kony and his Lord’s Resistance Army in Africa".

[24] Three and a half star reviewer for AllMusic, James Christopher Monger, states: "The 13-track set adds some relatively subtle flourishes of electronics to the mix while dialing back a little on Sean Mackin's signature violin playing, but fans looking to conjure up some nostalgia for the band's Ocean Avenue heyday will find what they're looking for on standout cuts like the catchy and propulsive 'Make Me So,' the big-hearted 'Transmission Home,' and rousing 'Deepest Well'.