My Dreams was Loveless's last release for Epic before the label closed its Nashville branch. The project was co-produced by Gordy and Justin Niebank. Contributing musicians included Lee Roy Parnell, Jon Randall, and Emmylou Harris. The album included four cover songs: Waylon Jennings's "Dreaming My Dreams with You", Richard Thompson's "Keep Your Distance", Steve Earle's "My Old Friend the Blues", and a duet with Dwight Yoakam on a cover of Delaney Bramlett's "Never Ending Song of Love". The cover of "Keep Your Distance" was the only single from the album. Brian Wahlert of Country Standard Time said of this album that Loveless and Gordy "have a knack for finding songs that express the joy and pain of everyday life in a way that anyone can relate to." He praised Loveless's vocal delivery on the song "On the Verge of Tears" in particular. Jack Bernhardt of The News and Observer considered the album her strongest release, noting the "storytelling intrigue" of the songs, while comparing Loveless's vocals favorably to those of Patsy Cline. The same year as this album, Vince Gill featured her as a duet partner on the track "Out of My Mind" from his compilation These Days. 2008–present: Continued Bluegrass work and semi-retirement 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