Castlepoint Cyber Security is an AI platform that provides data classification and risk management capabilities across enterprise environments. The platform analyzes content across multiple formats and locations without relying on metadata, enabling organizations to identify and classify sensitive, classified, or risky data. The system detects and labels Controlled Unclassified Information (CUI) and classified data based on content analysis. It identifies sensitive data including PII, PCI, and PHI, as well as special category sensitive data. The platform automatically determines appropriate security labels for documents and emails and can push these labels to Microsoft Purview for data loss prevention controls. Castlepoint maps civil and criminal penalties associated with potential data spills and provides visibility into legislative secrecy obligations. The platform uses regular expression and ontology-based detection to apply secrecy, information handling, and privacy obligations across systems. The system includes user behavior monitoring with high-fidelity event tracking across systems. It provides alerts for actionable events such as new sensitive data detection or access to high-risk records via Copilot. The platform supports retention policy management for lawful disposal of risky data. Organizations can manage organization-specific risks such as intellectual property or audit data. The platform provides enterprise-wide visibility of operations, assets, and individuals over time, addressing dark data challenges by identifying what data exists, where it resides, and who interacts with it.