Ashleigh Casebolt is a proud Oklahoman whose passion for the legal field has guided every step of her academic and professional journey. She began her legal education at Rose State College and then transferred to Tulsa Community College, where she earned her Associate of Arts in Paralegal Studies and graduated with honors in December 2023. With a strong foundation in legal research, writing, and procedural knowledge, Ashleigh is continuing to drive that growth forward as she pursues her Bachelor of Science in Legal Studies with a minor in Criminal Justice at Northeastern State University, where she is also completing Law & Paralegalism Certificates I and II. She is expected to graduate with highest honors in May 2026.
Ashleigh’s professional journey began in personal injury law, where she spent two years at a busy and highly respected Tulsa firm. There, she supported nine attorneys throughout the full litigation process, managed a substantial caseload, and gained experience that many paralegals encounter much later in their careers. Her work in personal injury law strengthened her ability to analyze complex facts, communicate compassionately with clients in crisis, and manage high-volume work with precision and reliability.
Today, Ashleigh brings that same dedication to Diana Cupps Law, where she is an invaluable member of the team. She works closely with the attorneys to move cases forward efficiently and ensure that clients receive the support and information they need during some of the most challenging moments in their lives. In addition to her work in family law, Ashleigh assists medical malpractice matters, applying her personal injury background. Her calm professionalism, strong communication skills, and ability to explain legal processes clearly and compassionately make her a trusted point of contact for many clients.
Ashleigh’s leadership extends beyond the office. She currently serves as Secretary of the Tulsa County Bar Association Paralegal Section, where she helps organize continuing education programs, supports professional networking, and contributes to the advancement of the paralegal field. Her involvement in the TCBA reflects her commitment not only to her own development but also to strengthen the legal community around her.
Known for her strong work ethic, dedication to learning, and drive for continuous improvement, Ashleigh hopes to attend law school in the future. Her goal is to become an attorney who serves Oklahoma families with knowledge, empathy, and unwavering commitment. She aspires to develop specialized expertise, mentor future legal professionals, and make a meaningful, lasting impact on the legal field.
Outside of her academic and professional responsibilities, Ashleigh enjoys spending time with her three dogs - her pug Meatball, her chihuahua Street, and her Akita puppy Bucky. She also loves reading and spending quality time with her loved ones. This balance supports the focus and resilience she applies to her legal career.
Driven, compassionate, and committed to continuous growth, Ashleigh brings both professionalism and heart to every role she takes on and every client she helps. She is honored to be part of the team at Diana Cupps Law and looks forward to the many opportunities ahead in her legal career.