In 2006, Loveless appeared on rock singer Bob Seger's Face the Promise as a duet partner on the track "The Answer's in the Question". David N. Cole, Seger's audio engineer, had recommended Loveless as a duet partner because he thought the song should be recorded as a duet. Seger was initially unsure if Loveless would approve, but the two agreed after realizing they were fans of each other's music. She then took a hiatus from recording, due in part to Epic closing its Nashville branch. In addition, her mother and mother-in-law had both died and her brother Roger had suffered a stroke. Her next album release was Sleepless Nights on Saguaro Road Records in 2008. According to an interview with CMT, Loveless chose to do a covers album dedicated to both Roger and to her sister Dottie (who died in 1996). Gordy produced and played bass on the album, with other contributors including pianist Hargus "Pig" Robbins, guitarist Al Perkins, and drummer Harry Stinson. The album featured covers of songs first cut by The Everly Brothers, George Jones, Porter Wagoner, and Webb Pierce. The lead single was a cover of Jones's "Why Baby Why". Jonathan Keefe 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.
