She was a researcher and attorney of the Chicago Law Enforcement Study Group, Northwestern University Center for Urban Affairs from 1972 to 1973, and a supervising attorney of Northwestern University School Law Legal Aid Clinic from 1973 to 1974.
She was in private practice in San Francisco, California from 1983 to 1991, serving as senior counsel to Pacific Bell from 1990 to 1991.
[2] On June 27, 1991, Caulfield was nominated by President George H. W. Bush to a seat on the United States District Court for the Northern District of California vacated by Judge William Schwarzer.
She was confirmed by the United States Senate on October 31, 1991, and received her commission on November 5, 1991.
[2] Caulfield thereafter returned to private practice in San Francisco, and continued to lecture at Stanford until her death on November 9, 2010.