Playbook Objectives:
- To identify and exploit vulnerabilities in a web application belonging to a hypothetical company.
- To improve the defensive strategies and response protocols of the security team.
- To raise awareness about the importance of securing web applications against cyber threats.
- To define clear and actionable remediation steps to prevent real-world exploits of similar nature.
Difficulty Level:
- Advanced
Scenario:
- Company Name: DataSecure Insurance, Inc.
- Business Type: Insurance and Financial Services
- Assets Involved:
- Corporate Website: Customer portal for insurance services (datasecure-insurance.com)
- Internal Employee Portal: Used for managing policies and customer data
- Network Infrastructure:
- On-premises data center hosting web servers, application servers, and databases
- Use of third-party cloud services hosted on AWS for some insurance quoting functions
- Employee Persona: John Doe, Senior IT Security Analyst at DataSecure Insurance, Inc.
- Attack Story:
- John Doe has been noticing an increase in targeted phishing campaigns against DataSecure’s employees, raising concerns that an adversary might be profiling the company for weaknesses.
- DataSecure launches a new customer-facing web application designed to streamline policy management, attracting attention from both new customers and potential threat actors.
- There has been an uptick in publicized breaches within the financial sector, putting pressure on DataSecure to ensure the robustness of their cybersecurity defenses.
- The company board mandates a comprehensive Cyber Range exercise to test and improve the security of their web application infrastructure.
Category:
- Web Application Security
- Penetration Testing
Exercise Attack Steps:
- Reconnaissance:
- Use tools such as Nmap, OWASP Amass, or Shodan to gather information about DataSecure’s public-facing web infrastructure.
- Enumerate subdomains, IP ranges, and identify potential entry points for the attack.
- Vulnerability Scanning:
- Conduct an automated scan using tools like OWASP ZAP or Nessus to detect common vulnerabilities (SQL injection, cross-site scripting, etc.) in the web app.
- Analyze the results to prioritize potential exploit vectors.
- Exploitation:
- Attempt to exploit discovered vulnerabilities using manual methods or tools such as SQLmap, Metasploit, etc.
- Document successful exploitation techniques and capture proof of concept for each vulnerability.
- Post-Exploitation:
- Explore the file system, escalate privileges if possible, and assess the potential for data exfiltration.
- Mimic an attacker’s actions post-compromise to identify what data could be accessed or stolen.
- Privilege Escalation:
- Perform tasks to escalate privileges on the webserver or the surrounding infrastructure—check for misconfigured permissions or vulnerable service configurations.
- Data Exfiltration:
- Demonstrate the potential for sensitive data theft by securely copying data without exposing actual customer information.
- Maintaining Access:
- Illustrate ways an attacker could maintain persistence on the compromised system using web shells or malicious service installations.
- Covering Tracks:
- Detail methods used to clear logs and evade detection that would simulate an attacker’s steps to remain unnoticed.
- Incident Response:
- Implement an incident response scenario requiring John Doe and his team to identify, contain, and eradicate the simulated breach.
- Reporting and Remediation:
- Compile a detailed report outlining the weaknesses found, the methods used to exploit them, and offer guidance on strengthening the company’s web application defense measures.
- Follow up with a meeting between the IT security team and the company board to discuss strategic changes to the security posture that accommodate the Cyber Range exercise findings.
- Lessons Learned:
- Assess the effectiveness of the exercise and provide feedback on the incident response actions.
- Arrange for a training workshop based on the exercise to cover identified security gaps and enhance the security team’s skills.
