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The Caroline County Sheriff's Department (CCSD) is the primary law enforcement agency servicing 32,617 people within 320.14 square land miles (829.2 km2) and over 472 square miles of roadway within Caroline County, Maryland.

The current sheriff is John "Randy" Bounds. The CCSO is divided into seven divisions:

Patrol Division- is responsible for handling 9-1-1 calls, traffic enforcement, accident control, community relations, and other incidents deemed appropriate by authority.

Criminal Investigations Division (CID)- is responsible for handling the investigation of felonious crimes such as murder, sex offenses, Controlled Dangerous Substances (illicit drugs), etc.

K-9 Division- the K-9 division is responsible for patrol, narcotics investigation, and tracking personnel.

Court Security Division- is responsible for ensuring the security of the courthouse and the surrounding areas as well as maintaining courtroom decor.

Teen Court Division- is responsible for the juvenile cases that are directed away from the court system to utilize an alternative method of correcting minor violations by juveniles aged 10–18.

Civil Process Division- is responsible for enforcing processes of the court system such as domestic violence protective/peace orders, civil paper service, and criminal summonses.

Records Division- is a mainly civilian support section that is responsible for maintain records of fingerprinting, arrest reports, crime reports, and other court processes such as warrants, summonses, and protective orders.