"Try" was released as the album's second single worldwide and lead single in United States on June 9, 2014, and a lyric video was released the following day featuring fans, as well as female celebrities such as Hoda Kotb, Miranda Lambert, Sara Bareilles, Katharine McPhee and the members of Fifth Harmony without makeup. The official video shows Caillat along with other women with makeup, which they remove later on in the video. On July 2 she released a lyric-video for "Live It Up". The official lyric-video for "Never Gonna Let You Down" was released on October 25. The fourth album, Gypsy Heart, was released only on September 30, and was produced by American record producer Babyface. It features songwriting collaborations with past co-writer, Jason Reeves, as well as new co-writers and producers Max Martin, Julian Bunetta, and Johan Carlsson. The album debuted at No. 17 on the Billboard 200 for chart dated October 18, 2014, with 16,000 copies sold in the first week. The album has sold 91,000 copies in the United States as of October 2016.
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 The Walking Dead: Songs of Survival Vol. 2 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.