'I've Got That Old Feeling' was her first album to rise onto the Billboard charts, getting to the top seventy-five on the country chart. The single from it "Steel Rails" was her first single tracked by Billboard getting to number 73 position. The title single "I've Got That Old Feeling" was the first song for which she recorded a music video.
Krauss' second album 'Everytime You Say Goodbye' was released in 1992 winning her second Grammy for Best Bluegrass Album of the year. She then joined the show Grand Ole Opry in 1993. At the age of 21 she was the youngest cast member and the first bluegrass artist to join the show in twenty-nine years. She also worked on a project with the Cox Family in 1994, a bluegrass album called I Know Who Holds Tomorrow.
In 1995 she released 'Now That I've Found You: A Collection', a compilation of older releases and some covers of her favorite works by other artists, was released in 1995. Some of these covers include Bad Company's "Oh Atlanta," The Foundations' "Baby, Now That I've Found You," and The Beatles' "I Will."
The single "When You Say Nothing at All" reached number three on the Billboard country chart; the album peaked in the top fifteen on the all-genre Billboard 200 chart, and sold two million copies to become Krauss' first double-platinum album. Krauss also was nominated for and won four Country Music Association Awards.