After earning her Bachelor of Science in Nursing from St. John College of Cleveland in 1970, Diana Kupchella accepted a commission in the U.S. Air Force Nurse Corps. She served on active duty from 1971 to 1997 in a variety of stateside and foreign assignments including Chief Nurse in Okinawa, a Fellowship with Senator Daniel Inouye of Hawaii in Washington, D.C., and Director of Medical Inquiries and Information in the Office of the Air Force Surgeon General.

Post service, Diana graduated from Law School at George Mason University and was admitted to the Virginia Bar in 2000. Diana worked on Capitol Hill as Democratic Counsel for the Senate Committee on Indian Affairs until 2005. 

Currently, she serves as President of the Virginia Council of Chapters and President for the Northern Virginia Chapter of the Military Officers Association of America and Secretary of the Chesapeake Nurse Attorneys, Inc.