By the mid 90s, Montgomery put his career on hold due to a vocal coral injury. Within months he was back on form, producing pop-orientated albums which did not do as well as his country albums. In 2004, he signed with Warner Bros. With Warner Bros, he produced several fairly successful albums. In 2008, Montgomery founded his record label, Springtown Records. That same year, he released his first album from the label. That album was called, Time Files.