Coaching Career
While at Morton, Frail began to become involved in coaching, firstly under Peter Cormack then former team-mate at Hearts Dave McPherson. He retired from his playing role at the end of the 2001–02 season and became a full-time assistant to Morton's third manager within the year, John McCormack. McCormack was sacked in 2004, and Frail and the rest of the coaching staff left with him. Later that year, after attending Hearts UEFA Cup tie with Sporting Braga, he was invited to join their coaching staff by then manager Craig Levein. Initially coach of the under-19 side, he was promoted to become assistant coach when John McGlynn left to manage Raith Rovers in 2006.
Frail, along with sporting director Anatoly Korobochka, took temporary charge of Hearts' first team in March 2007 after the departure of Valdas Ivanauskas. It was confirmed in June 2007 that Frail and Korobochka would take charge of the Jambos for the 2007–08 season with Bulgarian Angel Chervenkov coming in as assistant, though it was left ambiguous which one of the pair had responsibility for team selection. After poor form, which saw Hearts drop to tenth in the SPL, Frail was promoted to caretaker manager in January 2008 as the club planned to appoint a new permanent manager. It was announced Frail will be replaced as manager at the end of the 2007/08 season.
In April 2009, Stephen was appointed the coach of Celtic's under-19 team.
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