Krauss' second Union Station album "Every Time You Say Goodbye" was released in 1992, and she went on to win her second Grammy Award for Best Bluegrass Album of the year. She then joined the Grand Ole Opry in 1993 at the age of 21. She was the youngest cast member at the time, and the first bluegrass artist to join the Opry in twenty-nine years. She also collaborated on a project with the Cox Family in 1994, a bluegrass album called "I Know Who Holds Tomorrow". Mandolin and guitar player Dan Tyminski replaced Tim Stafford in Union Station in 1994. Late in the year, Krauss recorded with the band Shenandoah on its single "Somewhere in the Vicinity of the Heart", which brought her to the country music Top Ten for the first time and it won the Grammy Award for Best Country Collaboration with Vocals. Also in 1994, Krauss collaborated with Suzy Bogguss, Kathy Mattea, and Crosby, Stills, and Nash to contribute "Teach Your Children" to the AIDS benefit album Red Hot + Country produced by the Red Hot Organization. In 1997, she recorded vocals and violin for "Half a Mind", on Tommy Shaw's 7 Deadly Zens album.