Abigail Caudill began her career in 1998 as a correctional officer at the Kentucky State Reformatory, and then transferred to Roederer Correctional Complex (RCC). In 2000 she was promoted to classification and treatment officer for the Assessment Center at RCC. 

Later in 2000, Caudill transferred to Probation and Parole, serving as a probation and parole officer in multiple counties. In 2005 she went back to RCC managing the minimum-security unit and the substance abuse program. In 2006 she promoted to unit administrator I and in 2007 to unit administrator II. In 2012 she promoted to program administrator for the Assessment Center at RCC. 

In 2015, Caudill was promoted to deputy warden at Blackburn Correctional Complex. During her time there, she has overseen programs/operations and security. In 2020, she was named acting warden, and then in 2021 she was appointed as warden. 

Caudill was one of the original master trainers for the department's case management tool and served as an institutional trainer for the offender management system. In 2014 she earned her certification as an auditor for the Prison Rape Elimination Act. She is a member of the Kentucky Council on Crime and Delinquency. Caudill served as president from 2016-17 and has served on the state board as the membership chair/assistant to the treasurer. 

A 1998 graduate of Murray State University, Caudill is a graduate of the 2012 Commissioner's Leadership Program and served as a mentor in 2023.