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 1989-90, and as a member of the Hartford County Bar Association she served as treasurer from 1993-94 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 1980's.

Since her appointment to the bench, Judge DiPentima's assignments have included presiding judge of the Hartford New Britain Housing Session, 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.

On May 13, 2003, Judge DiPentima was sworn in as a judge of the Appellate Court.