Comprehensive Penetration Test Report for Art’s Tailor Shoppe

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Situation:

The objective of this project was to consolidate findings from individual penetration test exercises conducted on the Art’s Tailor Shoppe network. These tests assessed vulnerabilities across various systems, applications, and configurations, providing a comprehensive security evaluation before the launch of the shop’s web application.

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Obstacles:

1. Complex System Landscape:
   • Multiple interconnected systems and services required detailed analysis to identify vulnerabilities.
2. Diverse Attack Vectors:
   • A mix of outdated software, insecure configurations, and weak security policies were exploited.
3. Data Sensitivity:
   • Ensuring responsible handling of sensitive data throughout the testing process.

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Actions Taken:

1. Reconnaissance:
   • Used tools like nmap, fierce, and Nessus to scan and map the network.
   • Identified open ports, outdated software, and misconfigured services.
2. Exploitation:
   • Exploited vulnerabilities like VSFTPD backdoors, buffer overflows, weak password practices, and hardcoded credentials.
   • Used Metasploit modules, privilege escalation techniques, and social engineering to demonstrate risks.
3. Privilege Escalation:
   • Demonstrated full Domain Admin access and captured sensitive data like encryption keys and admin credentials.
4. Analysis and Reporting:
   • Documented findings, risks, and mitigation strategies for each identified vulnerability.

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Results:

1. Critical Risks Identified:
   • Persistent threats such as the EternalBlue exploit, weak passwords, and unpatched software.
2. Sensitive Data Exfiltrated:
   • Admin credentials, session tokens, and encryption keys were retrieved.
3. Comprehensive Recommendations Provided:
   • A detailed roadmap to address vulnerabilities, including software updates, stronger policies, and user training.

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Tool Purpose Overview:

Tools and Their Roles:

• nmap: Mapped the network and identified open ports and services.
• fierce: Performed DNS reconnaissance to discover hidden subdomains.
• Metasploit: Exploited vulnerabilities like EternalBlue and backdoors.
• Nessus: Scanned for known vulnerabilities across systems.
• John the Ripper: Cracked weak passwords using leaked hash databases.
• Chisel & Proxychains: Created SOCKS proxies for internal network exploration.
• BeEF: Used for browser-based social engineering and session token exfiltration.

General Skillset:

• Demonstrated advanced penetration testing skills, including privilege escalation, social engineering, and report writing.

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Recommendations:

1. Update and Patch Systems:
   • Ensure all software is updated to the latest versions.
2. Harden Security Configurations:
   • Implement HTTPS universally, disable unused services, and enforce strong password policies.
3. Conduct Regular Training:
   • Educate employees on identifying phishing and social engineering attacks.
4. Implement Robust Monitoring:
   • Use intrusion detection systems (IDS) and conduct regular vulnerability scans.

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