From 1979 to 1981, she worked as a staff attorney for Connecticut Legal Services Inc. in Willimantic, Connecticut, representing low income persons in domestic disputes (especially spousal abuse and custody issues) and housing disputes. In 1981, she joined the Hartford law firm of Moller, Horton & Fineberg, P.C., and in 1985 she became a principal in the firm. While associated with the firm from 1981 through 1993, she litigated products liability and other personal injury actions at the trial court level and enjoyed an active appellate advocacy practice. In November 1993, Governor Lowell Weicker appointed Judge DiPentima to the trial bench as a Superior Court judge.

During her years of practice, she was an active member of the Connecticut Bar Association, serving as president of the Young Lawyers Section from 1989 to 1990, and as a member of the Hartford County Bar Association she served as treasurer from 1993 to 1994 and as a director from 1990 to 1993. Each year, she has written two chapters of annotations for the Connecticut Practice Book Annotated (West) since the late 1980s.

Since her appointment to the bench, Judge DiPentima's assignments have included presiding judge of the Hartford and New Britain Housing Divisions, presiding judge in Meriden, and, from 1998 to 2003, Administrative Judge of the judicial district of Litchfield. She has served on the Rules Committee and the Judicial Education Committee. From 2001 to 2002, she served as president of the Connecticut Judges Association. In 2010, Judge DiPentima received the Connecticut Bar Association’s Henry J. Naruk Judiciary Award.

On May 13, 2003, Judge DiPentima was sworn in as a judge of the Appellate Court. In June of 2007, Chief Justice Chase Rogers appointed her to serve as chair of the newly-formed Public Service and Trust Commission, which created a five-year strategic plan for the Judicial Branch. She continues to oversee the implementation of the Judicial Branch strategic plan. On March 29, 2010, Judge DiPentima was sworn in as Chief Judge of the Appellate Court by Chief Justice Rogers.