Caroline Cleveland (b. 1987), of Suffern, New York, served as an officer in the United States Army from 2009-2013. From 2011-2012 she was a part of a the all-female Cultural Support Team who worked alongside Army Rangers on night combat raids in Afghanistan. Caroline Elizabeth Cleveland was born 7 October 1987 in Suffern, New York, and spent her adolescence in East Greenbush, New York, outside of Albany. After graduating from Bishop McGinn High School in 2005, Cleveland began attending Siena College in Albany that fall, and signed a contract for the United States Reserve Officer Training Corps (ROTC), which meant after four years of college, she would be required to perform four years of active duty service and four years of reserve duty service.

During college Cleveland participated in two-weeks of Air Assault School at Fort Pickett, Virginia. This training included three phases: first, basic helicopter knowledge; second, learning to inspect sling lines; and third, completing a rappel out of a helicopter. The training culminated with a twelve-mile ruck march. Two days before graduating from college in 2009, Cleveland was commissioned into the U.S. Army, and chose Military Occupational Specialty (MOS) 31A, or Military Police (MP).

A week after graduation, Cleveland left for active duty training at Fort Lewis, Washington, where she had the opportunity to work on the Leadership Reaction Course Committee, evaluating cadets on their leadership performance. She was then sent to Fort Sill, Oklahoma, for six weeks of Basic Officer Leadership Course II (BOLC II), and then to Fort Leonard Wood, Missouri, for ten weeks of Basic Officer Leadership Course III (BOLC III). During BOLC III, Cleveland received training on crowd/riot control and learned military police doctrine. The training culminated with a ten-day field exercise. When she completed her trainings, Cleveland requested to be assigned to Germany, because she thought being closer to Iraq and Afghanistan would afford her the opportunity to be deployed, although in the end it did not.

In January 2010, Cleveland was sent to a non-deployable unit at United States Army Garrison Heidelberg, Germany. As a 2nd lieutenant, she was assigned to the 529th MP Company. Shortly before her eighteen-month tour was due to end, Cleveland received an email requesting volunteers for Cultural Support Teams (CSTs), who would be tasked with developing trust-based relationships with the Afghan women who may be encountered during military patrols. Cleveland submitted the necessary paperwork and was accepted to the program. In May 2011, Cleveland returned to the U.S., and was sent to Fort Bragg, North Carolina, for CST assessment and selection. During one-hundred hours of training, Cleveland participated in a ruck march, as well as a psychological evaluation.

After learning she had been accepted into the program, Cleveland was sent to Contiguous U.S. (CONUS) Replacement Center (CRC) at Fort Benning, Georgia. Here, she finalized standard deployment requirements, such as receiving vaccinations and creating a will, and completed six weeks of Pashtun language and culture education. In August 2011, Cleveland deployed to Kandahar, Afghanistan, and embedded with the army's 75th Ranger Regiment. When she arrived, Cleveland learned there were women there already doing CST tasks, although they had just been pulled from the regular ranks and never properly trained. These women instructed the new CSTs on their responsibilities during missions, which included accompanying Ranger Strike Forces on night raids, and, with the help of interpreters, searching and safeguarding the Afghan women, while also tactically questioning them. During eight months in Afghanistan, Cleveland was involved in three firefights with insurgents.

After deployment, Cleveland returned to Fort Bragg, and participated in a debriefing that would help form a curriculum for future CSTs. Cleveland was then assigned back to Germany and the Military Police Company, where she supervised the S-3 Training and Operations Shop. Over the course of a year, she planned and executed two mission readiness exercises for platoons within the battalion that were deploying She was also promoted to captain. She then returned to Fort Bragg, and eventually separated from the army in 2013. In August 2015, Cleveland began a Doctor of Physical Therapy degree program at the University of North Carolina at Chapel Hill, with the intention of working with war survivors, veterans, and people affected by genocide in countries around the world. She graduated in 2018.