Operators, not auditors.

Deep Woods Security is a boutique offensive security firm based in Virginia Beach. We specialize in penetration testing, red team operations, and AI security for organizations where failure isn't an option.

Senior operators. Direct engagement.

Engagements are scoped and executed by the same people who deliver findings. No handoffs to junior analysts. No automated scan dumps dressed up as penetration tests.

We maintain a limited client roster. This allows for deeper familiarity with each environment and faster response when priorities shift.

Federal roots. Offensive focus.

Our team brings direct experience from federal cybersecurity operations. We've developed cyber test plans for Navy ship systems, conducted red team operations on federal healthcare contracts, and built offensive capabilities for organizations that take security seriously.

This background shapes how we work. We understand compliance requirements, but we focus on actual threats. We know how federal programs operate, and we know how adversaries think about breaking them.

Active TS/SCI clearance. SAM.gov registered. Ready for the work that requires both.

Cleared. Registered. Operational.

Active TS/SCI clearance with full scope polygraph eligibility. SAM.gov registered (UEI: S122EB1T51C6) for federal contracting. Virginia LLC established October 2024.

Methodology aligned with NIST 800-115, PTES, and OWASP testing standards.

Where We've Operated

Federal Healthcare Red Team

Active red team operations on federal healthcare contracts. Mythic C2 deployment, adversary emulation mapped to MITRE ATT&CK, and assumed-breach scenarios for large-scale environments.

Navy Cyber Test Planning

Cyber test plan development for OPTEVFOR including CVN-78 Cyber Survivability testing. OSINT, passive reconnaissance, and red team objective definition for Navy ship systems.

Defense Contractor Support

Security consulting and RFP response support for Hampton Roads defense contractors. Technical writing and strategy for Navy cybersecurity contracts.

Network Defense Operations

IDS/IPS monitoring and incident response across federal network infrastructure. ACAS vulnerability analysis and STIG compliance reporting.

Virginia Beach, VA

Based in the Hampton Roads region, adjacent to the largest concentration of Navy facilities on the East Coast. We serve clients nationally but maintain deep roots in the defense community.

NAICS Codes

  • 541512 — Computer Systems Design Services
  • 541519 — Other Computer Related Services
  • 541690 — Other Scientific and Technical Consulting

Ready to work together?

Whether you need penetration testing, red team operations, or strategic advisory, we'd like to hear about what you're working on.

Get in Touch