of Slant Magazine called Loveless's vocals "interpretive" while also noting the "deliberate thematic heft" of the songs chosen. Jurek wrote of this album, "Loveless treats these songs without even a trace of nostalgia, but as the living embodiment of stories that not only transfer emotion, but reveal the hidden truths of love, life, sadness, grief, and wisdom gained by experience." In addition to this album, she sang duet vocals on the track "House of Cash" from George Strait's 2008 album Troubadour. At the 51st Annual Grammy Awards, Sleepless Nights was nominated for Best Country Album, while "House of Cash" was nominated for Best Country Collaboration with Vocals. A year later, Loveless released her last studio album to date called Mountain Soul II. This was a follow-up to the original Mountain Soul project. Like its predecessor, it featured influences of acoustic and bluegrass music. Vince Gill, Del McCoury, and Emmylou Harris were among the contributing vocalists, the latter doing so on a cover of her own "Diamond in My Crown". Loveless also included a number of traditional Christian songs such as "Children of Abraham", which she sang a cappella. Loveless chose to include Christian material on the project as she had previously sung "Amazing Grace" with Ralph Stanley and Emmylou Harris while on tour with them. The album's lead single was a cover of Harlan Howard's "Busted". Keefe praised individual tracks such as this and the rendition of "I'm Working on a Building", but otherwise thought the album lacked the "focus" of its predecessor. Although she largely retired from performing in 2009, Loveless has sporadically contributed to other artists' albums. She provided vocals to the track "Dear Diamond" on Miranda Lambert's 2010 album Four the Record. The same year, she joined with Danica Patrick, Caitlyn Jenner, and Michael Strahan in a program started by NASCAR titled Drive, which was done to raise awareness of chronic obstructive pulmonary disease. Loveless chose to join the program as her sister Dottie had died of the disease. She also appeared on albums by Angaleena Presley, Elizabeth Cook, Trisha Yearwood, and Carly Pearce. In October 2022, Loveless was one of several performers at Kentucky Rising, a benefit concert held at Rupp Arena to raise funds for victims of flooding in Kentucky. Other performers at the venue included Chris Stapleton, Dwight Yoakam, Ricky Skaggs, and Tyler Childers. A month later, Loveless and Stapleton performed "You'll Never Leave