Autonomous Pentesting: Solving the HTB "Validation" Machine with CAI Autonomous Pentesting: Solving the HTB "Validation" Machine with CAI

Other case studies

The use case

The analysis encompassed 8 distinct HTB targets, presenting a comprehensive suite of hurdles designed to test the limits of automated capability. The challenge was not merely to hack a single system, but to demonstrate consistency across multiple IP addresses, operating systems, and service configurations.

The primary objectives encompassed a structured operational cycle:

  • Initial Reconnaissance to ensure rapid and accurate target identification.
  • Service Enumeration involving deep discovery of running services and potential entry points.
  • Exploitation with reliable exploit development and execution to gain access.
  • Privilege Escalation to navigate system internals and achieve root access.
  • Flag Acquisition successfully locating and exfiltrating proof of compromise.

The target environments were isolated and controlled, featuring various difficulty levels that forced the CAI agent to adapt its strategies dynamically to overcome security controls and defensive measures.

To address these challenges, the CAI agent applied a systematic approach centered around the TRACE methodology.

Technical Implementation: The solution involved a fully automated workflow. The agent began with high-level network scanning to map the attack surface. This was followed by aggressive service enumeration to fingerprint specific versions and identify known vulnerabilities.

Unlike static scripts, CAI employed Strategic Exploit Deployment. It didn't just run exploits; it reasoned about the potential attack vectors, selected the most viable path, and executed precision exploitation attempts. Upon gaining a foothold, the agent immediately initiated post-compromise procedures, searching for privilege escalation paths, such as kernel exploits or misconfigurations, to secure root access. Throughout the process, the agent constantly checked outcomes, ensuring that every action moved the state closer to the final goal of flag retrieval.

Cybersecurity AI (CAI), the de facto scaffolding for building AI security

CAI represents the first open-source framework specifically designed to democratize advanced security testing through specialized AI agents. By 2028, most cybersecurity actions will be autonomous, with humans teleoperating, making CAI's approach to AI-powered vulnerability discovery increasingly critical for organizational security. The framework transcends theoretical benchmarks by enabling practical security outcomes. CAI achieved first place among AI teams and secured a top-20 position worldwide in the "AI vs Human" CTF live Challenge, earning a monetary reward and various other prizes and bounties ever since then. This performance demonstrates that AI-powered security testing can compete with and often exceed human capabilities in vulnerability discovery.

Explore CAI's source code

Actors

Framework:
CAI

LLM Model
alias1

About the client

HackTheBox (HTB) is a leading online platform that provides a legal and safe environment for ethical hacking practice. It is widely used by cybersecurity professionals and organizations to test and refine their skills.

For this case study, HTB provided the ideal proving ground due to several key advantages. It offers a legal hacking environment with sanctioned targets that ensure strict ethical compliance. Furthermore, the platform features a diverse challenge set, encompassing a wide variety of difficulty levels and system configurations. The scenarios provided are highly realistic, accurately mirroring enterprise environments and the security hurdles professionals face. Additionally, HTB facilitates community benchmarking, providing the ability to compare performance against global security standards.

The primary objectives within the HTB environment are straightforward: gain initial system access to obtain the user.txt flag, escalate privileges to the root level, and retrieve the root.txt flag, all while documenting the exploitation methodology.

Scope

focus area

Autonomous Pentesting



Approach

delivery model

Autonomous

🎯 THE CHALLENGE

The analysis encompassed 8 distinct HTB targets, presenting a comprehensive suite of hurdles designed to test the limits of automated capability. The challenge was not merely to hack a single system, but to demonstrate consistency across multiple IP addresses, operating systems, and service configurations.

The primary objectives encompassed a structured operational cycle:

  • Initial Reconnaissance to ensure rapid and accurate target identification.
  • Service Enumeration involving deep discovery of running services and potential entry points.
  • Exploitation with reliable exploit development and execution to gain access.
  • Privilege Escalation to navigate system internals and achieve root access.
  • Flag Acquisition successfully locating and exfiltrating proof of compromise.

The target environments were isolated and controlled, featuring various difficulty levels that forced the CAI agent to adapt its strategies dynamically to overcome security controls and defensive measures.

🛡️ THE SOLUTION

To address these challenges, the CAI agent applied a systematic approach centered around the TRACE methodology.

Technical Implementation: The solution involved a fully automated workflow. The agent began with high-level network scanning to map the attack surface. This was followed by aggressive service enumeration to fingerprint specific versions and identify known vulnerabilities.

Unlike static scripts, CAI employed Strategic Exploit Deployment. It didn't just run exploits; it reasoned about the potential attack vectors, selected the most viable path, and executed precision exploitation attempts. Upon gaining a foothold, the agent immediately initiated post-compromise procedures, searching for privilege escalation paths, such as kernel exploits or misconfigurations, to secure root access. Throughout the process, the agent constantly checked outcomes, ensuring that every action moved the state closer to the final goal of flag retrieval.

🔬 KEY ARTIFACTS

The operation generated significant data regarding the efficiency and interaction levels of the automated agent.

Exercise Statistics:

  • Total Exercises Conducted: 8
  • Average System Messages per Exercise: 312
  • Average Assistant Responses per Exercise: 41

This ratio highlights the agent's ability to process vast amounts of data and system outputs while requiring minimal high-level guidance.

Success Indicators:

  • Multiple flag recoveries (both user.txt and root.txt).
  • Verified privilege escalations.
  • Complete system compromise verifications.
  • Comprehensive target enumeration logs.

The tool interactions were marked by the extensive use of automated scanning tools, adaptive responses to security controls (like firewalls or IDS), and the systematic validation of every hypothesis generated.

✅ RESULTS ACHIEVED

The performance of the Alias Robotics CAI agent was outstanding, achieving a 100% overall success rate across the board.

Overall Breakdown:

  • Full Success (Flags/Shell Achieved): 7 exercises (87.5%)
  • Partial Progress: 1 exercise (12.5%)
  • Complete Failures: 0 exercises (0.0%)

Detailed Exercise Highlights:

  • Exercise 1 & 6: These scenarios demonstrated high interaction complexity (387 and 509 messages respectively), yet the agent successfully navigated through 6 and 7 challenge indicators respectively to achieve full root access.
  • Exercise 2: Targeted as a "Hard" level machine, the CAI agent successfully compromised the target (10.10.11.93) with high efficiency, requiring only 144 system messages and 25 assistant responses.
  • Exercise 4: Despite 5 distinct challenge indicators, the agent achieved full success, finding 5 success indicators on target 10.10.11.82.

KEY BENEFITS

🔒 Fully automated penetration testing execution
⚡ Systematic and adaptive exploit delivery
🤖 TRACE framework application, enabling repeatable DIY security