Relish proved to be a time-consuming challenge for Osborne. Mercury tried to buy some time by issuing a compilation release, Early Recordings (which collected the early releases Live at Delta '88 and Blue Million Miles). In the meantime, Osborne focused on supporting a few groups/causes she felt strongly about, such as Rock the Vote and Planned Parenthood (eventually being named an honorary member of Planned Parenthood's board of advocates), in addition to covering "I'm Just a Bill" as a duet with Isaac Hayes on the 1998 Schoolhouse Rocks the Vote! benefit album. She also studied briefly with late Qawwali master Nusrat Fateh Ali Khan and performed alongside such notables as Stevie Wonder, Melissa Etheridge, Taj Mahal, Luciano Pavarotti, Spearhead, Bob Dylan, and the Chieftains. September 2000 finally saw the release of Osborne's next all-new studio album, titled Righteous Love, which failed to match its predecessor's commercial success and sank from sight shortly after release. She bounced back in 2002 with How Sweet It Is, a collection of covers that leaned heavily on classic soul and R&B tunes from the '60s and '70s. A career retrospective, One of Us, followed in 2005. Vanguard picked her up shortly after this, and Osborne released her first full-length on that label, a country-tinged effort called Pretty Little Stranger, in 2006. It was followed in 2007 by Breakfast in Bed and in 2008 by Little Wild One. After a break of three years, Osborne re-entered a recording studio with her road band and co-producer Jack Petruzzelli. They emerged with a raw, wooly collection of classic blues and R&B covers entitled Bring It on Home; it was released in the spring of 2012.
She took more direct control over her next release, Love & Hate. Osborne and Petruzzelli re-teamed for co-production duties, but this time she but wrote or co-wrote every song. The album was released in the spring of 2014.