The project started in September 2007, when W.P.A began to record songs for an upcoming album release. In Sara Watkins' December 2007 MySpace blog, she said "we're hoping to nearly (finish) the record in the next few days. We're tracking live and trying to get as much down at one time as possible. It is a very satisfying way to record".[4]
Their self-titled release debuted on August 28, 2009. Some of the tracks from the self-titled debut include the Phillips-penned tracks "Rise Up", "You Will Always Have My Love", and "End This Now", as well as a Luke Bulla/Glen Phillips collaboration entitled "Cry For You". "Not Sure", one of three Sean Watkins track that is featured, was originally released on the Fiction Family album. The Works Progress Administration version features Luke Bulla giving a rich voice to the melody as well as the fuller orchestration.