Caillat co-wrote "Chasing the Sun" along with Jason Reeves and Toby Gad for Hilary Duff. The song was released as the first single for Duff's fifth album. Caillat penned a song for "" called "The Way I Was" which was included exclusively for the Walmart version of the soundtrack album. On June 9, 2014, Republic Records released "Try", written by Caillat, Babyface and Jason Reeves and was produced by Babyface. The song was released as her lead single on her fifth studio album, "Gypsy Heart". Caillat says about "Try", "It's this song I've had in my head my entire life about personal insecurities, imperfections, self-confidence issue." The song hit number 55 on the Billboard Hot 100 in August of that year and later went on platinum in USA.