Following his return from Vietnam, Rupert worked full time in the Ohio Governor's Office for Governor John J. Gilligan and at the end of Gilligan's term, worked for Attorney General William J. Brown. While working at both the Governor's Office and the Attorney General's Office, Rupert attended law school at Capital University in Columbus, Ohio, and graduated with a Juris Doctorate Degree in 1976. Rupert then returned to Franklin and began practicing at Ruppert, Bronson & Ruppert. Further, Rupert has served as Judge of Franklin Municipal Court since 2006 and will be retiring at the end of 2018.
Since returning to Franklin after law school, Rupert has remained actively involved in Franklin area activities. He served on the Franklin City School Board for sixteen years and as a Franklin Township Trustee for ten years. Rupert has also been a member of the Franklin Civil Service Commission, Franklin Merger Commission, Franklin City Pool Board, Joint Emergency Medical Services Board and Franklin City Planning Commission. Rupert was President of the Franklin Area Chamber of Commerce, the Franklin Rotary Club and the Warren County Bar Association. In 1993, Rupert was chosen Citizen of the Year by the Franklin Area Chamber of Commerce and in 1986 was named the State Campaign Manager for Senator John Glenn's successful re-election campaign. He is also a member of the Franklin High School Hall of Fame.
In 2002, Rupert was honored by being named to the Ohio Veterans Hall of Fame and was appointed as a member of its Executive Committee from 2002 through 2005. Additionally, Rupert served as a volunteer trustee for the Deardoff Senior Citizen Center and Memorial Trust from 1996 to 2005.