Following the band's previous album "Croftwork" (2005) and its subsequent supporting tour, the band were quick to work on "What Men Deserve to Lose", and the gap between the albums is to date the shortest between any of the band's albums. In addition to new member Stafford, the brass section The Wayward Boys return from the previous album. The band had numerous sources of inspiration on the album, including taking inspiration from their surroundings in Skye, and people and places they had encountered in the years prior to making the album. The album was released to a positive reception from music critics, and two concerts from the subsequent supporting tour also formed the basis of the band's sole live album, "Live" (2009).